Synthesis 2013; 45(8): 1000-1015
DOI: 10.1055/s-0032-1318475
short review
© Georg Thieme Verlag Stuttgart · New York

Hydrocinnamic Acids: Application and Strategy of Synthesis

Sergei M. Korneev*
Further Information

Publication History

Received: 08 October 2012

Accepted after revision: 25 February 2013

Publication Date:
19 March 2013 (online)


On the occasion of the 150th anniversary of the first synthesis of hydrocinnamic acid

Abstract

This review summarizes all the main approaches to the synthesis of hydrocinnamic acids based on the construction of the side chain with a carboxy moiety around the aromatic ring. Numerous methods for the synthesis of hydrocinnamic acids by constructive or destructive routes, such as reductive or oxidative reactions, rearrangements, catalytic reactions, or electrochemical conversion, are considered and presented in a rational system.

 
  • References

  • 1 Previous address: Institute of Chemistry, Sankt Petersburg State University, University prosp. 26, Sankt Petersburg 198504, Russian Federation; E-mail: sergei.korneev@gmx.de
  • 2 Erlenmeyer E, Aleksejeff P. Justus Liebigs Ann. Chem. 1862; 121: 375
    • 3a Aleksejeff (Alekseev) Piotr Petrovitch (1840–1891), a Russian chemist who investigated, in particular, the properties of azo compounds and developed the method of azoxybenzene synthesis.
    • 3b Richard August Carl Emil Erlenmeyer (1825–1909), an outstanding German chemist. His achievements, for example, see: Das Portrait: Emil Erlenmeyer 1825–1909: Krätz O. Chem. Unserer Zeit 1972; 6: 53
    • 4a Erlenmeyer E. Z. Chem. Pharm. 1863; 307
    • 4b Erlenmeyer E. Justus Lieb. Ann. Chem. 1866; 137: 327

      For example, see:
    • 5a Cocker JD, Halsall TG, Bowers A. J. Chem. Soc. 1956; 4259
    • 5b De Pascual TJ, Urones JG, Marcos IS, Nunez L, Basabe P. Phytochemistry 1983; 22: 2805
    • 5c Matsuda H, Ando S, Kato T, Morikawa T, Yoshikawa M. Bioorg. Med. Chem. 2006; 14: 138

      For example, see:
    • 6a Moss CW, Lambert MA, Goldsmith D. J. Appl. Microbiol. 1970; 19: 375
    • 6b Pino JA, Queris O. J. Agric. Food Chem. 2011; 59: 4885
    • 6c Häser K, Wenk HH, Schwab W. J. Agric. Food Chem. 2006; 54: 6236
    • 6d Burger BV, Smit D, Spies HS. C, Schmidt C, Schmidt U, Telitsina AY. J. Chem. Ecol. 2001; 27: 1277
    • 6e Wirz B, Doswald S, Kupfer E, Wostl W, Weisbrod T, Estermann H In Asymmetric Catalysis on Industrial Scale . Blaser H.-U, Schmidt E. Wiley-VCH; Weinheim: 2004: 385
  • 7 Boros EE, Cowan DJ, Cox RF, Mebrahtu MM, Rabinowitz MH, Thompson JB, Wolfe III LA. J. Org. Chem. 2005; 70: 5331
    • 8a Srinivasan CV, Johar PS, Wadhwa L. WO 2008035381, 2008 ; Chem. Abstr. 2008, 148, 379220.
    • 8b Drüeke TB, Ritz E. Clin. J. Am. Soc. Nephrol. 2009; 4: 234
  • 9 Kornev AB, Peregudov AS, Martynenko VM, Balzarini J, Hoorelbekec B, Troshin PA. Chem. Commun. 2011; 47: 8298
  • 10 Stauffer SR, Hartwig JF. J. Am. Chem. Soc. 2003; 125: 6977
  • 11 Yang D, Wang H.-L, Sun Z.-N, Chung N.-W, Shen J.-G. J. Am. Chem. Soc. 2006; 128: 6004
  • 12 Izzo I, De Caro S, De Riccardis F, Spinella A. Tetrahedron Lett. 2000; 41: 3975
  • 13 Belletire JL, Fry DF. J. Org. Chem. 1988; 53: 4724
  • 14 Krishnamurty HG, Ghosh S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1986; 25: 411
  • 15 Maitra U, Bag BG, Rao P, Powell D. J. Chem. Soc., Perkin Trans. 1 1995; 2049
  • 16 Cholli AL, Kumar R, Canteenwala T, Kumar V. US 20080249335, 2008 ; Chem. Abstr. 2008, 149, 449121.

    • Examples of application of various catalysts:
    • 17a AlCl3: Matveeva ED, Podrugina TA, Morozkina NYu, Zefirova ON, Seregin IV, Bachurin SO, Pellicciari R, Zefirov NS. Russ. J. Org. Chem. 2002; 38: 1769 ; Zh. Org. Khim. 2002, 38, 1830
    • 17b H2SO4: Kim SH, Kim YM, Lee HS, Kim JN. Tetrahedron Lett. 2010; 51: 1592
    • 17c Polyphosphoric acid: Shavva AG, Antimonova OI, Baigozin DV, Starova GL, Selivanov SI, Morozkina SN. Russ. J. Org. Chem. 2010; 46: 1511 ; Zh. Org. Khim. 2010, 46, 1506
    • 17d Methanesulfonic acid: Banwell MG, Stewart SG. Org. Prep. Proced. Int. 2002; 34: 177
    • 17e HF: Brouwer DM, van Doorn JA, Kiffen AA, Kramer PA. Recl. Trav. Chim. Pays-Bas. 1974; 93: 189
    • 17f ClSO3H: Taylor JG, Correia CR. D. J. Org. Chem. 2011; 76: 857
  • 18 Yajima N, Hiroki Y, Yoshino H, Koizumi T. WO 2007049812, 2007 ; Chem. Abstr. 2007, 146, 481911.
    • 19a Zhdanov RI, Corey EJ. Steroids 2009; 74: 723
    • 19b Huisman HO. Angew. Chem. 1971; 83: 511
  • 20 Gu Y, Xue K. Tetrahedron Lett. 2010; 51: 192
  • 21 Sugumaran M, Dali H, Kundzicz H, Semensi V. Bioorg. Chem. 1989; 17: 443
  • 22 Adediran SA, Cabaret D, Lohier J.-F, Wakselman M, Pratt RF. Bioorg. Med. Chem. 2010; 18: 282
  • 23 Judd KE, Mahon MF, Caggiano L. Synthesis 2009; 2809
    • 24a Dohi T, Uchiyama T, Yamashita D, Washimi N, Kita Y. Tetrahedron Lett. 2011; 52: 2212
    • 24b Volod’kin AA, Malysheva RD, Ershov VV. Russ. Chem. Bull. 1982; 31: 1454 ; Izv. Akad. Nauk SSSR, Ser. Khim. 1982, 1633
  • 25 Zawada PV, Banfield SC, Kerr MA. Synlett 2003; 971
  • 26 Lutz GP, Du H, Gallagher DJ, Beak P. J. Org. Chem. 1996; 61: 4542
  • 27 Fichter F, Senti R. Chem. Zentralbl. 1927; 98: 54
  • 28 Fichter F, Schlager E. Helv. Chim. Acta 1927; 10: 406
  • 29 Nagakubo K, Iwakura Y, Takei K, Okada T. Nippon Kagaku Zasshi 1957; 78: 1209 ; Chem. Abstr. 1960, 54, 28179
  • 30 Shaver FW. US 2587540, 1952 ; Chem. Abstr. 1952, 46, 57376.
  • 31 Olivier M, Marechal E. Bull. Soc. Chim. Fr. 1974; 699
  • 32 Kawashima M, Sato T, Fujisawa T. Tetrahedron 1989; 45: 403
  • 33 Hopff H. DE 666466, 1932 ; Chem. Abstr. 1939, 33, 14329.
    • 34a Zukerwanik IP, Terent’ewa IV. Dokl. Akad. Nauk SSSR. 1945; 50: 257 ; Chem. Abstr. 1949, 43, 24983
    • 34b Sato K, Lin Y.-S, Amakasu T. Bull. Chem. Soc. Jpn. 1969; 42: 2600
  • 35 Normant JF, Alexakis A, Cahiez G. Tetrahedron Lett. 1980; 21: 935
  • 36 Wei Z, Matla AS, Romo D. Org. Lett. 2007; 9: 2111
  • 37 Smith ND, Wohlrab AM, Goodman M. Org. Lett. 2005; 7: 255
  • 38 Davisson VJ, Poulter CD. J. Am. Chem. Soc. 1993; 115: 1245
    • 39a O’Brien EM, Bercot EA, Rovis T. J. Am. Chem. Soc. 2003; 125: 10498
    • 39b Jensen AE, Kneisel F, Knochel P. Org. Synth. 2002; 79: 35
  • 40 Cooke Jr MP. J. Org. Chem. 1987; 52: 5729
  • 41 Aurell MJ, Domingo LR, Mestres R, Muñoz E, Zaragozá RJ. Tetrahedron 1999; 55: 815
    • 42a Job A, Reich R. C. R. Hebd. Seances Acad. Sci. 1924; 179: 330
    • 42b Terao J, Tomita M, Singh SP, Kambe N. Angew. Chem. Int. Ed. 2010; 49: 144
  • 43 Yamashita K, Chatani N. Synlett 2005; 919
    • 44a Lemhadri M, Doucet H, Santelli M. Tetrahedron 2004; 60: 11533
    • 44b Djakovitch L, Pinel C. Curr. Org. Synth. 2009; 6: 54
    • 44c Kim H.-S, Lee S.-J, Choi B, Yoon CM. Synthesis 2012; 44: 3161
    • 44d Miura K, Tomita M, Ichikawa J, Hosomi A. Org. Lett. 2008; 10: 133
    • 44e Höfling SB, Hultsch C, Wester H.-J, Heinrich MR. Tetrahedron 2008; 64: 11846
    • 44f Métay E, Léonel E, Sulpice-Gaillet C, Nédélec J.-Y. Synthesis 2005; 1682
    • 44g Vautravers NR, Breit B. Synlett 2011; 2517
    • 44h Horiguchi H, Tsurugi H, Satoh T, Miura M. J. Org. Chem. 2008; 73: 1590
    • 44i Navarre L, Martinez R, Genêt J.-P, Darses S. J. Am. Chem. Soc. 2008; 130: 6159
    • 44j Noël T, Gök Y, Van der Eycken J. Tetrahedron: Asymmetry 2010; 21: 540
    • 44k Tasnádi G, Winkler CK, Clay D, Sultana N, Fabian WM. F, Hall M, Ditrich K, Faber K. Chem. Eur. J. 2012; 18: 10362
    • 44l Eriksson B, Kurz G, Hedberg C, Westman J. WO 2008090356, 2008 ; Chem. Abstr. 2008, 149, 200905.
    • 44m De Azambuja F, Correia CR. D. Tetrahedron Lett. 2011; 52: 42
    • 45a Marvel CS. Org. Synth. 1941; 21: 99
    • 45b Young DD, Torres-Kolbus J, Deiters A. Bioorg. Med. Chem. Lett. 2008; 18: 5478
    • 45c Kawasaki M, Goto M, Kawabata S, Kometani T. Tetrahedron: Asymmetry 2001; 12: 585
    • 45d Mahulikar PP, Mane RB. J. Chem. Res. 2006; 12
    • 45e Rotthaus O, LeRoy S, Tomas A, Barkigia KM, Artaud I. Eur. J. Inorg. Chem. 2004; 1545
    • 45f Yamamoto K, Fukushima H, Yumioka H, Nakazaki M. Bull. Chem. Soc. Jpn. 1985; 58: 3633
    • 45g Sarac AS, Ozgul SE, Faltz H, Gencturk A, Gilsing H.-D, Schulz B. J. Nanosci. Nanotechnol. 2010; 10: 8043
    • 45h Yadav JS, Reddy BV. S, Mishra AK. Chem. Lett. 2010; 39: 280
    • 46a Carter RH, Colyer RM, Hill RA, Staunton J. J. Chem. Soc., Perkin Trans. 1 1976; 1438
    • 46b Sharma AK, Subramani AV, Gorman CB. Tetrahedron 2007; 63: 389
    • 46c Fillion E, Zorzitto AK. J. Am. Chem. Soc. 2009; 131: 14608
    • 46d Devel L, Garcia S, Czarny B, Beau F, Lajeunesse E, Vera L, Georgiadis D, Stura E, Dive V. J. Biol. Chem. 2010; 285: 35900
    • 47a Kruse LI, Kaiser C, DeWolf Jr WE, Chambers PA, Goodhart PJ, Ezekiel M, Ohlstein EH. J. Med. Chem. 1988; 31: 704
    • 47b Mochizuki A, Nagata T, Kanno H. WO 2008123017, 2008 ; Chem. Abstr. 2008, 149, 471467.
    • 47c Batt DG, Qiao JX, Modi DP, Houghton GC, Pierson DA, Rossi KA, Luettgen JM, Knabb RM, Jadhav PK, Wexler RR. Bioorg. Med. Chem. Lett. 2004; 14: 5269
    • 48a Porter J, Dykert J, Rivier J. Int. J. Pept. Protein Res. 1987; 30: 13
    • 48b Ananthanawat C, Banphavichit V, Vilaivan T. Synth. Commun. 2006; 36: 1845
    • 48c Fillion E, Wilsily A. J. Am. Chem. Soc. 2006; 128: 2774
    • 48d Hillier MC, Desrosiers J.-N, Marcoux J.-F, Grabowski EJ. J. Org. Lett. 2004; 6: 573
    • 48e Musso DL, Cochran FR, Kelley JL, McLean EW, Selph JL, Rigdon GC, Orr GF, Davis RG, Cooper BR, Styles VL, Thompson JB, Hall WR. J. Med. Chem. 2003; 46: 399
    • 48f Marianacci O, Micheletti G, Bernardi L, Fini F, Fochi M, Pettersen D, Sgarzani V, Ricci A. Chem. Eur. J. 2007; 13: 8338
    • 48g Fallan C, Quigley PF, Lam HW. J. Org. Chem. 2011; 76: 4112
    • 48h Miyata K, Kutsuna H, Kawakami S, Kitamura M. Angew. Chem. Int. Ed. 2011; 50: 4649
    • 49a Matsuo J.-i, Sasaki S, Hoshikawa T, Ishibashi H. Chem. Commun. 2010; 46: 934
    • 49b Andrews SP, Ladlow M. J. Org. Chem. 2003; 68: 5525
    • 49c Kwart H, Gaffney A. J. Org. Chem. 1983; 48: 4502
    • 50a Peter MG, Merz A. Tetrahedron: Asymmetry 1995; 6: 839
    • 50b Bailly J, Hertel C, Hunziker D, Lerner C, Obst Sander U, Peters J.-U, Pflieger P, Schulz-Gasch T. WO 2009040288, 2009 ; Chem. Abstr. 2009, 150, 374301.
    • 50c Ballester M, Veciana J, Riera J, Castaner J, Rovira C, Armet O. J. Org. Chem. 1986; 51: 2472
    • 50d Chaturvedi S, Otteson K, Bergot J. Tetrahedron Lett. 1999; 40: 8205
    • 50e Skibinski D, Jain S, Singh M, O’Hagan D. WO 2011084549, 2011 ; Chem. Abstr. 2011, 155, 211853.
    • 51a Yang X, Fox T, Berke H. Chem. Commun. 2011; 47: 2053
    • 51b Duhamel P, Duhamel L, Danvy D, Monteil T, Lecomte J.-M, Schwartz J.-C. EP 729936, 1996 ; Chem. Abstr. 1996, 125, 275420.
    • 51c Ramachary DB, Venkaiah C, Reddy YV, Kishor M. Org. Biomol. Chem. 2009; 7: 2053
    • 51d Ramachary DB, Mondal R, Venkaiah C. Eur. J. Org. Chem. 2010; 3205
    • 52a Stambuli JP, Stauffer SR, Shaughnessy KH, Hartwig JF. J. Am. Chem. Soc. 2001; 123: 2677
    • 52b Beak P, Selling GW. J. Org. Chem. 1989; 54: 5574
    • 52c Luisi R, Capriati V, Florio S, Vista T. J. Org. Chem. 2003; 68: 9861
    • 53a El AliB, Vasapollo G, Alper H. J. Org. Chem. 1993; 58: 4739
    • 53b Ojima I, Tsai C.-Y, Tzamarioudaki M, Bonafoux D. Org. React. 2000; 56: 1
    • 53c Neumann H, Brennfuehrer A, Beller M. Adv. Synth. Catal. 2008; 350: 2437
    • 53d Ruiz N, del Rio I, Jimenez JL, Claver C, Fornies-Camer J, Cardin CC. J, Gladiali S. J. Mol. Catal. A: Chem. 1999; 143: 171
    • 53e Brunet J.-J, Neibecker D, Srivastava RS. Tetrahedron Lett. 1993; 34: 2759
    • 54a Hoberg H, Peres Y, Milchereit A. J. Organomet. Chem. 1986; 307: C38
    • 54b Lapidus AL, Eliseev OL, Stepin NN, Bondarenko TN. Russ. Chem. Bull. 2004; 53: 2564 ; Izv. Akad. Nauk. Ser. Khim. 2004, 53, 2458
    • 54c Eliseev OL, Stepin NN, Bondarenko TN, Lapidus AL. Dokl. Chem. 2005; 401: 59 ; Dokl. Akad. Nauk., 2005, 401, 486
    • 54d Noskov YuG, Petrov ES. Russ. J. Gen. Chem. 2000; 70: 1585 ; Zh. Obsh. Khim., 2000, 70, 1685
    • 54e Estorach CT, Orejon A, Ruiz N, Masdeu-Bulto AM, Laurenczy G. Eur. J. Inorg. Chem. 2008; 3524
    • 54f Senboku H, Komatsu H, Fujimura Y, Tokuda M. Synlett 2001; 418
    • 54g Ohmiya H, Tanabe M, Sawamura M. Org. Lett. 2011; 13: 1086
    • 55a Louie J, Bielawski CW, Grubbs RH. J. Am. Chem. Soc. 2001; 123: 11312
    • 55b Taniguchi T, Sugiura Y, Zaimoku H, Ishibashi H. Angew. Chem. Int. Ed. 2010; 49: 10154
    • 55c Lee JT, Alper H. Tetrahedron Lett. 1991; 32: 1769
    • 55d Duñach E, Périchon J. J. Organomet. Chem. 1988; 352: 239
    • 55e Yuan G.-Q, Jiang H.-F, Lin C. Tetrahedron 2008; 64: 5866
    • 56a Monflier E, Mortreux A. J. Mol. Catal. 1994; 88: 295
    • 56b Francalanci F, Gardano A, Foá M. J. Organomet. Chem. 1985; 282: 277
    • 56c Lin Y.-S, Yamamoto A. Bull. Chem. Soc. Jpn. 1998; 71: 723
    • 56d Takeuchi R, Tsuji Y, Fujita M, Kondo T, Watanabe Y. J. Org. Chem. 1989; 54: 1831
    • 57a Polyzos A, O’Brien M, Petersen TP, Baxendale IR, Ley SV. Angew. Chem. Int. Ed. 2011; 50: 1190
    • 57b Maclean MJ, Walker S, Wang T, Eichinger PC. H, Sherman PJ, Bowie JH. Org. Biomol. Chem. 2010; 8: 371
    • 57c Ochiai H, Jang M, Hirano K, Yorimitsu H, Oshima K. Org. Lett. 2008; 10: 2681
    • 57d Pickering RE, Wysocki MA, Eisenbraun EJ. J. Labelled Compd. Radiopharm. 1985; 22: 837
    • 57e Yabe O, Mizufune H, Ikemoto T. Synlett 2009; 1291
    • 57f McNulty J, Nair JJ, Cheekoori S, Larichev V, Capretta A, Robertson AJ. Chem. Eur. J. 2006; 12: 9314

      Examples of synthesis of cinnamic acids by the palladium-catalyzed Heck-type reaction, see:
    • 58a Singh P, Das D, Prakash O, Singh AK. Inorg. Chem. Acta 2013; 394: 77
    • 58b Ulaganatha Raja M, Ramesh R, Liu Y. Tetrahedron Lett. 2011; 52: 5427
    • 58c Felpin F.-X, Nassar-Hardy L, Le Callonnec F, Fouquet E. Tetrahedron 2011; 67: 2815

    • Knoevenagel reactions:
    • 58d Simonyan AV. Pharm. Chem. J. 1993; 27: 92 ; Khim.-Farm. Zh.; 1993, 27, 21
    • 58e McDonald IM. Name React. Homol. 2009; 474

    • Wittig condensations:
    • 58f Galatsis P. Name React. Homol. 2009; 588
    • 59a Takahashi T, Miyazawa M. Pharmazie 2010; 65: 913
    • 59b Kankan RN, Rao DR, Birari DR, Curtis PA. WO 2010100429, 2010 ; Chem. Abstr. 2010, 153, 382679.
    • 59c Jurčík V, Nolan SP, Cazin CS. J. Chem. Eur. J. 2009; 15: 2509
    • 59d Ratheesh KumarV. K, Gopidas KR. Tetrahedron Lett. 2011; 52: 3102
    • 59e Namdu K, Min SK, Cheon MP, Jaiwook P. Tetrahedron Lett. 2004; 45: 7057
    • 59f Ikawa T, Sajiki H, Hirota K. Tetrahedron 2005; 61: 2217
    • 59g Solodenko W, Wen H, Leue S, Stuhlmann F, Sourkouni-Argirusi G, Jas G, Schönfeld H, Kunz U, Kirschning A. Eur. J. Org. Chem. 2004; 3601
    • 59h Brunel JM. Tetrahedron 2007; 63: 3899
    • 59i Kumar V, Sharma A, Sinha AK. Helv. Chim. Acta 2006; 89: 483
    • 60a Adkins H, Billica HR. J. Am. Chem. Soc. 1948; 70: 695
    • 60b Charlton JL, Lai HK, Lypka GN. Can. J. Chem. 1980; 58: 458
    • 60c Nesloney CL, Kelly JW. J. Org. Chem. 1996; 61: 3127
    • 60d Lee J.-T, Alper H. Tetrahedron Lett. 1990; 31: 1941
    • 60e Fernández-Pérez H, Donald SM. A, Munslow IJ, Benet-Buchholz J, Maseras F, Vidal-Ferran A. Chem. Eur. J. 2010; 16: 6495
    • 60f Li J.-Q, Quan X, Andersson PG. Chem. Eur. J. 2012; 18: 10609
    • 60g Minnaard AJ, Feringa BL, Lefort L, de Vries JG. Acc. Chem. Res. 2007; 40: 1267
    • 60h Qiu L, Li Y.-M, Kwong FY, Yu W.-Y, Fan Q.-H, Chan AS. C. Adv. Synth. Catal. 2007; 349: 517
    • 60i Imamoto T, Tamura K, Zhang Z, Horiuchi Y, Sugiya M, Yoshida K, Yanagisawa A, Gridnev ID. J. Am. Chem. Soc. 2012; 134: 1754
    • 60j Balogh S, Farkas G, Madarász J, Szöllősy A, Kovács J, Darvas F, Ürge L, Bakos J. Green Chem. 2012; 14: 1146
    • 60k Zhu S.-F, Yu Y.-B, Li S, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2012; 51: 8872
    • 61a Ghosh S, Datta I, Chakraborty R, Das TK, Sengupta J, Sarkar DC. Tetrahedron 1989; 45: 1441
    • 61b Youssef A.-HA, Sharaf SM, Abdel-Baki SA. J. Prakt. Chem. 1982; 324: 491
    • 61c Hahn FL, Schleipen R. Z. Anorg. Allg. Chem. 1926; 153: 97
    • 61d Schwenk E, Papa D, Whitman B, Ginsberg HF. J. Org. Chem. 1944; 9: 175
    • 61e Nose A, Kudo T. Chem. Pharm. Bull. 1990; 38: 2097
    • 61f Kamochi Y, Kudo T. Chem. Lett. 1993; 1495
    • 61g Karrer P, Yen Y, Reichstein I. Helv. Chim. Acta 1930; 13: 1311
    • 62a Keinan E, Perez D. J. Org. Chem. 1987; 52: 2576
    • 62b Khurana JM, Sharma P. Bull. Chem. Soc. Jpn. 2004; 77: 549
    • 62c Nose A, Kudo T. Chem. Pharm. Bull. 1990; 38: 1720
    • 62d Genthner BR. S. Biodegradation 1999; 10: 27
    • 62e Whiting GC, Carr JG. Nature (London) 1959; 184: 1427
    • 62f Hulley ME, Toogood HS, Fryszkowska A, Mansell D, Stephens GM, Gardiner JM, Scrutton NS. ChemBioChem 2010; 11: 2433
    • 63a Marie C. C. R. Hebd. Seances Acad. Sci. 1903; 136: 1331
    • 63b Deronzier A. J. Chim. Phys. Phys.-Chim. Biol. 1989; 86: 31
    • 63c Rosca S, Ungureanu M, Stan R. Rev. Roum. Chim. 1996; 41: 91
    • 63d Ingersoll AW. Org. Synth. 1929; 9: 42
    • 63e Chiba T, Okimoto M, Nagai H, Takata Y. Bull. Chem. Soc. Jpn. 1983; 56: 719
    • 63f Coche L, Moutet J.-C. J. Am. Chem. Soc. 1987; 109: 6887
    • 63g Wilson, Trans. Electrochim. Soc. 1947, 92, 369.
    • 63h Norris JF, Cummings EO. Ind. Eng. Chem. 1925; 17: 305
    • 64a Rosenmund KW, Zetzsche F. Chem. Ber. 1918; 51: 578
    • 64b Kurita T, Aoki F, Mizumoto T, Maejima T, Esaki H, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2008; 14: 3371
    • 64c Counsell RE, Longino MA, Weichert JP, Schwendner SP. US 4873075, 1989 ; Chem. Abstr. 1990, 112, 216456.
    • 64d Broadbent HS, Campbell GC, Bartley WJ, Johnson JH. J. Org. Chem. 1959; 24: 1847
    • 64e Ma J, Novack A, Nashashibi I, Pham P, Rabbat CJ, Song J, Shi DF, Zhao Z, Choi Y.-J, Chen X. WO 2010048207, 2010 ; Chem. Abstr. 2010, 152, 525859.
    • 64f Larsen SD, Barf T, Liljebris C, May PD, Ogg D, O’Sullivan TJ, Palazuk BJ, Schostarez HJ, Stevens FC, Bleasdale JE. J. Med. Chem. 2002; 45: 598
    • 64g Glaser C. Justus Liebigs Ann. Chem. 1867; 143: 325
    • 64h Rappoport Z, Gazit A. J. Am. Chem. Soc. 1987; 109: 6698
    • 65a Mathieu CR. Hebd. Seances Acad. Sci. 1938; 206: 1387
    • 65b Lawrence NJ, Brown S. Tetrahedron 2002; 58: 613
    • 65c Srinivasan CV, Johar PS, Wadhwa L. WO 2008035381, 2008 ; Chem. Abstr. 2008, 148, 379220.
    • 65d Khurana JM, Kandpal BM, Kukreja G, Sharma P. Can. J. Chem. 2006; 84: 1019
    • 65e Yoshikawa N, Yamada YM. A, Das J, Sasai H, Shibasaki M. J. Am. Chem. Soc. 1999; 121: 4168
    • 66a Carnazzi E, Aumelas A, Barberis C, Guillon G, Seyer R. J. Med. Chem. 1994; 37: 1841
    • 66b Saikia A, Barthakur MG, Boruah RC. Synlett 2005; 523
    • 66c Pasto DJ, Taylor RT. Org. React. 1991; 40: 91
    • 66d Shen R, Chen T, Zhao Y, Qiu R, Zhou Y, Yin S, Wang X, Goto M, Han L.-B. J. Am. Chem. Soc. 2011; 133: 17037
    • 66e Málek J. Org. React. 1988; 36: 249
    • 66f Imamoto T, Mita T, Yokoyama M. J. Org. Chem. 1987; 52: 5695
    • 66g Concellon JM, Rodriguez-Solla HM, Concellon C. Tetrahedron Lett. 2004; 45: 2129
    • 67a Hattori K, Sajiki H, Hirota K. Tetrahedron 2001; 57: 4817
    • 67b Weis M, Breuninger D, Ebel K, Winsel H. WO 2010012675, 2010 ; Chem. Abstr. 2010, 152, 238600.
    • 67c Stefane B, Polanc S. Tetrahedron 2009; 65: 2339
    • 67d Padhi SK, Chadha A. Synlett 2003; 639
    • 67e Kamochi Y, Kudo T, Masuda T, Takadate A. Chem. Pharm. Bull. 2005; 53: 1017
    • 68a Takemoto T, Yasuda K, Ley SV. Synlett 2001; 1555
    • 68b Sedelmeier J, Ley SV, Baxendale IR, Baumann M. Org. Lett. 2010; 12: 3618
    • 68c ten Brink G.-J, Vis J.-M, Arends IW. C. E, Sheldon RA. J. Org. Chem. 2001; 66: 2429
    • 68d Krow GR. Org. React. 1993; 43: 251
    • 68e Mannam S, Sekar G. Tetrahedron Lett. 2008; 49: 1083
    • 68f Lim M, Yoon CM, An G, Rhee H. Tetrahedron Lett. 2007; 48: 3835
    • 68g de la Fuente G, Perestelo F, Rodriguez-Perez A, Falcon MA. Appl. Environ. Microbiol. 1991; 57: 1275
    • 69a de Vries JD, Roelfes G, Green R. Tetrahedron Lett. 1998; 39: 8329
    • 69b Hayashi M, Kawabata H, Yoshimoto K, Tanaka T. Phosphorus, Sulfur Silicon Relat. Elem. 2007; 182: 433
    • 69c Raj IV. P, Sudalai A. Tetrahedron Lett. 2005; 46: 8303
    • 69d Sohn SS, Bode JW. Org. Lett. 2005; 7: 3873
    • 69e Muller AJ, Bowers JS. Jr, Eubanks JR. I, Geiger CC, Santobianco JG. WO 9908989, 1999 ; Chem. Abstr. 1999, 130, 196502.
    • 69f Brenna E, Fuganti C, Gatti FG, Parmeggiani F. Tetrahedron: Asymmetry 2009; 20: 2694
    • 70a Langenbeck W, Richter M. Chem. Ber. 1956; 89: 202
    • 70b Yakura T, Ozono A. Adv. Synth. Catal. 2011; 353: 855
    • 70c Shang Y, But TY. S, Togo H, Toy PH. Synlett 2007; 67
    • 70d Miura T, Nakashima K, Tada N, Itoh A. Chem. Commun. 2011; 47: 1875
    • 70e Hamamoto H, Suzuki Y, Yamada YM. A, Tabata H, Takahashi H, Ikegami S. Angew. Chem. Int. Ed. 2005; 44: 4536
    • 70f Mannam S, Sekar G. Synth. Commun. 2010; 40: 2822
    • 70g Karade NN, Tiwari GB, Huple DB. Synlett 2005; 2039
    • 70h Díaz-Oltra S, Carda M, Murga J, Falomir E, Marco JA. Chem. Eur. J. 2008; 14: 9240
    • 70i Hirano J.-i, Miyamoto K, Ohta H. Tetrahedron Lett. 2008; 49: 1217
    • 71a Oleynik AS, Kuprina TS, Pevneva NYu, Markov AF, Kandalintseva NV, Prosenko AE, Grigor’ev IA. Russ. Chem. Bull. 2007; 56: 1135 ; Izv. Akad. Nauk. Ser. Khim. 2007, 1094
    • 71b Imbach P, Kawahara E, Konishi K, Matsuura N, Miyake T, Ohmori O, Roesel J, Teno N, Umemura I. WO 2006021454, 2006 ; Chem. Abstr. 2006, 144, 274291.
    • 71c Popaj K, Guggisberg A, Hesse M. Helv. Chim. Acta 2000; 83: 3021
    • 71d Lima PC, Lima LM, Da Silva KC. M, Léda PH. O, De Miranda AL. P, Fraga CA. M, Barreiro EJ. Eur. J. Med. Chem. 2000; 35: 187
    • 71e Brown HC, Kulkarni SV, Khanna VV, Patil VD, Racherla US. J. Org. Chem. 1992; 57: 6173
    • 72a Mori K. Tetrahedron: Asymmetry 2005; 16: 685
    • 72b Studenov AR, Szalda DE, Ding Y.-S. Nucl. Med. Biol. 2003; 30: 39
    • 72c Ma D.-Y, Wang D.-X, Zheng Q.-Y, Wang M.-X. Tetrahedron: Asymmetry 2006; 17: 2366
    • 72d Yasukawa K, Hasemi R, Asano Y. Adv. Synth. Catal. 2011; 353: 2328
    • 72e Chudinov AV, Kuznetsova VE, Zasedatelev AS, Barsky VE. WO 2008127139, 2008 ; Chem. Abstr. 2008, 149, 493676.
    • 72f Chen Y.-C, Xue D, Deng J.-G, Cui X, Zhu J, Jiang Y.-Z. Tetrahedron Lett. 2004; 45: 1555
    • 73a Schwenk E, Papa D. J. Org. Chem. 1946; 11: 798
    • 73b McMillan FH, King JA. J. Am. Chem. Soc. 1948; 70: 4143
    • 73c Bonjoch J, Diaba F, Pagès L, Pérez D, Soca L, Miralpeix M, Vilella D, Anton P, Puig C. Bioorg. Med. Chem. Lett. 2009; 19: 4299
    • 74a Lehr RE, Kumar S, Cohenour PT, Jerina DM. Tetrahedron Lett. 1979; 20: 3819
    • 74b Schroth W, Andersch J. Synthesis 1989; 202
    • 75a McPhee WD, Klingsberg E. J. Am. Chem. Soc. 1944; 66: 1132
    • 75b Stevens CL, Sherr AE. J. Org. Chem. 1952; 17: 1228
    • 76a Kirmse W. Eur. J. Org. Chem. 2002; 2193
    • 76b Sudrik SG, Sharma J, Chavan VB, Chaki NK, Sonawane HR, Vijayamohanan KP. Org. Lett. 2006; 8: 1089
    • 76c Mei T.-S, Wang D.-H, Yu J.-Q. Org. Lett. 2010; 12: 3140
    • 76d Sudrik SG, Chavan SP, Chandrakumar KR. S, Pal S, Date SK, Chavan SP, Sonawane HR. J. Org. Chem. 2002; 67: 1574
    • 77a Thottumkara PP, Vinod TK. Org. Lett. 2010; 12: 5640
    • 77b Laschat S, Kunz H. J. Org. Chem. 1991; 56: 5883
    • 77c Muñoz-Hernández L, Soderquist JA. Org. Lett. 2009; 11: 2571
    • 77d Hadden MK, Blagg BS. J. J. Org. Chem. 2009; 74: 4697
    • 77e Ramachandran PV, Burghardt TE. Chem. Eur. J. 2005; 11: 4387
    • 78a García JM, González A, Kardak BG, Odriozola JM, Oiarbide M, Razkin J, Palomo C. Chem. Eur. J. 2008; 14: 8768
    • 78b Lee S, Lim CJ, Kim S, Subramaniam R, Zimmerman J, Sibi MP. Org. Lett. 2006; 8: 4311
    • 78c Kobayashi S, Tanaka H, Amii H, Uneyama K. Tetrahedron 2003; 59: 1547
    • 78d Brown MK, Corey EJ. Org. Lett. 2010; 12: 172
    • 78e Tommila K. Ann. Acad. Sci. Fenn., Ser. A 1936; 46: 83 ; Chem. Zentralbl. 1937, 108, 204
    • 79a Schueler G, Boland W, Lauchu R. WO 2002055480, 2002 ; Chem. Abstr. 2002, 137, 79228.
    • 79b Belmessieri D, Morrill LC, Simal C, Slawin AM. Z, Smith AD. J. Am. Chem. Soc. 2011; 133: 2714
    • 79c Ballini R, Curini M, Epifano FM, Marcotullio MC, Rosati O. Synlett 1998; 1049
    • 79d Kang S.-H, Joo C.-I, Kim S.-M, Han H.-Y, Yang J.-W. Tetrahedron Lett. 2011; 52: 502