Enamide Derivatives: Versatile Building Blocks for Total Synthesis

Thibaut Courant; Guillaume Dagousset; Géraldine Masson

doi:10.1055/s-0034-1378706

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(13): 1799-1856
DOI: 10.1055/s-0034-1378706

review

Enamide Derivatives: Versatile Building Blocks for Total Synthesis

Authors

Thibaut Courant

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France eMail: Geraldine.Masson@cnrs.fr
Guillaume Dagousset

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France eMail: Geraldine.Masson@cnrs.fr
Géraldine Masson*

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France eMail: Geraldine.Masson@cnrs.fr

Abstract

Alle Artikel dieser Rubrik

Abstract

Enamides and enecarbamates are versatile building blocks in organic synthesis. This review describes the development of enamide chemistry and the utility of the resulting products in the synthesis of a variety of important, biologically active molecules.

1 Introduction

2 Asymmetric Hydrogenation of Enamides

3 Monofunctionalization of Enamide Derivatives

3.1 Palladium-Catalyzed α-Functionalization of Enamide Derivatives

3.2 Ruthenium-Catalyzed β-Functionalization of Enamide Derivatives

4 Ionic Vicinal Difunctionalization of Enamide Derivatives

4.1 Tandem Difunctionalization of Enamide Derivatives

4.2 Cycloadditions

4.2.1 [4+2] Cycloadditions

4.2.2 [2+2] Cycloadditions

4.2.3 Cyclopropanation of Enamides

4.3 Other Pericyclic Reactions

4.3.1 Electrocyclization Reactions

4.3.2 Overman Rearrangement

4.4 Platinum-Catalyzed Vicinal Difunctionalization of Enamide Derivatives

5 Radical Vicinal Difunctionalization of Enamide Derivatives

6 Oxidative Vicinal Difunctionalization of Enamide Derivatives

7 N-Arylation of Enecarbamates

8 Conclusion

9 Ligand Glossary

Key words

enamide - total synthesis - alkaloid - hydrogenation - functionalization

Volltext

Referenzen

References

1a Matsubara R, Kobayashi S. Acc. Chem. Res. 2008; 41: 292
1b Carbery DR. Org. Biomol. Chem. 2008; 6: 3455
1c Nugent TC, El-Shazly M. Adv. Synth. Catal. 2010; 352: 753
1d Gopalaiah K, Kagan H. Chem. Rev. 2011; 111: 4599
1e Bernadat G, Masson G. Synlett 2014; 25: 2842

2a Hickmott PW. Tetrahedron 1982; 38: 1975
2b Stork G. Med. Res. Rev. 1999; 19: 370
2c Stork G. Tetrahedron 2011; 67: 9754

Also see:

2d Seebach D, Beck AK, Badine DM, Limbach M, Eschenmoser A, Treasurywala AM, Hobi R, Prikoszovich W, Linder B. Helv. Chim. Acta 2007; 90: 425

For a review on electrophilic and nucleophilic substitution and addition reactions of enamines, see:

2e Hickmott PW In The Chemistry of Enamines, Part 1 . Rappoport Z. John Wiley & Sons; New York: 1994. Chap. 14, 727
2f Enders D, Bettray W In Asymmetric Synthesis with Chemical and Biological Methods . Enders D, Jaeger K.-E. Wiley-VCH; Weinheim: 2007: 38

3 Stork G, Dowd SR. J. Am. Chem. Soc. 1963; 85: 2178
4 Mayr H. Chem. Eur. J. 2003; 9: 2209

5a Èervinka O In The Chemistry of Enamines, Part 1 . Rappoport Z. John Wiley & Sons; New York: 1994. Chap. 9, 467
5b Bélanger G, Doré M, Ménard F, Darsigny V. J. Org. Chem. 2006; 71: 7481

For a review covering asymmetric organocatalysis, see:

6a Dalko PI. Enantioselective Organocatalysis . Wiley–VCH; Weinheim: 2006
6b Asymmetric Organocatalysis. In Topics in Current Chemistry. Vol. 291. List B. Springer; New York: 2009

For selected reviews on enamine catalysis, see:

6c Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
6d Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
6e MacMillan DW. C. Nature (London) 2008; 455: 304
6f Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
6g Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
6h Jensen KL, Dickmeiss G, Jiang H, Albrecht L, Jørgensen KA. Acc. Chem. Res. 2012; 45: 248
6i Meninno S, Lattanzi A. Chem. Commun. 2013; 49: 3821

7a Kuranaga T, Sesoko Y, Inoue M. Nat. Prod. Rep. 2014; 31: 514
7b Yet L. Chem. Rev. 2003; 103: 4283

Selected examples, see:

7c Okamoto K, Sakagami M, Feng F, Togame H, Takemoto H, Ichikawa S, Matsuda A. Org. Lett. 2011; 13: 5240
7d Villa MV. J, Targett SM, Barnes JC, Whittingham WG, Marquez R. Org. Lett. 2007; 9: 1631
7e Mathieson JE, Crawford JJ, Schmidtmann M, Marquez R. Org. Biomol. Chem. 2009; 7: 2170
7f Wang X, Porco JA. J. Am. Chem. Soc. 2003; 125: 6040
7g Kuranaga T, Sesoko Y, Sakata K, Maeda N, Hayata A, Inoue M. J. Am. Chem. Soc. 2013; 135: 5467
7h Wang X, Porco JA. J. Org. Chem. 2001; 66: 8215; and reference cited

8a Tracey MR, Hsung RP, Antoline J, Kurtz KC. M, Shen L, Slafer BW, Zhang Y In Science of Synthesis . Vol. 21. Georg Thieme Verlag; Stuttgart: 2005: 415
8b Shen R, Porco JA. Org. Lett. 2000; 2: 1333

9a Horner L, Siegel H, Büthe H. Angew. Chem., Int. Ed. Engl. 1968; 7: 942
9b Knowles WS, Sabacky MJ. Chem. Commun. 1968; 1445

10a Kagan HB, Langlois N, Dang TP. J. Organomet. Chem. 1975; 114: 325
10b Sinou D, Kagan HB. Chem. Pharm. Bull. 1992; 40: 2894

11 Vineyard BD, Knowles WS, Sabacky MJ, Bachman GL, Weinkauff DJ. J. Am. Chem. Soc. 1977; 99: 5946
12 Gopalaiah K, Kagan HB. Chem. Rev. 2011; 111: 4599
13 Storace L, Anzalone L, Confalone PN, Davis W, Fortunak JM, Giangiordano M, Haley JrJ. J, Kamholz K, Li H.-Y, Ma P, Nugent WA, Parsons Jr RL, Sheeran PJ, Silverman CE, Waltmire RE, Wood CC. Org. Process Res. Dev. 2002; 6: 54

14a Burk MJ, Feaster JE, Harlow RL. Organometallics 1990; 9: 2653
14b Burk MJ. J. Am. Chem. Soc. 1991; 113: 8518

15a Crépy KV. L, Imamoto T. Adv. Synth. Catal. 2003; 345: 79
15b Johnson NB, Lennon IC, Moran PH, Ramsden JA. Acc. Chem. Res. 2007; 40: 1291

16a Harrison P, Meek G. Tetrahedron Lett. 2004; 45, 9277
16b Mickel SJ. EP 543780, 1993 ; Chem. Abstr. 1993, 119, 203630.

17 Zhu G, Zhang X. J. Org. Chem. 1998; 63: 9590
18 Zhang G.-Y, Pai C.-C, Chan AS. C. J. Am. Chem. Soc. 1998; 120: 5808
19 Kuwano R, Sato K, Kurokawa T, Karube D, Ito Y. J. Am. Chem. Soc. 2000; 122: 7614
20 Xia D, Zhang Z, Zhang X. Org. Lett. 1999; 1: 1679

21a Li W, Zhang X. J. Org. Chem. 2000; 65: 5871
21b Yan Y, Rajanbabu TV. Org. Lett. 2000; 2: 4137

22a Imamoto T, Watanabe J, Wada Y, Masuda H, Yamada H, Tsuruta H, Matsukawa S, Yamaguchi K. J. Am. Chem. Soc. 1998; 120: 1635
22b Gridnev ID, Yamanoi Y, Higashi N, Tsuruta H, Yasutake M, Imamoto T. Adv. Synth. Catal. 2001; 343: 118
22c Yamanoi Y, Imamoto T. J. Org. Chem. 1999; 64: 2988
22d Gridnev ID, Imamoto T. Organometallics 2001; 20: 545

23 Gridnev ID, Yasutake M, Higashi N, Imamoto T. J. Am. Chem. Soc. 2001; 123: 5268
24 O’Shea PD, Gauvreau D, Gosselin F, Hughes G, Nadeau C, Roy A, Schultz CS. J. Org. Chem. 2009; 74: 4547
25 Corey EJ, Gin DY, Kania RS. J. Am. Chem. Soc. 1996; 118: 9202
26 Singh J, Kronenthal DR, Schwinden M, Godfrey JD, Fox R, Vawter EJ, Zhang B, Kissick TP, Patel B, Mneimne O, Humora M, Papaioannou CG, Szymanski W, Wong MK. Y, Chen CK, Heikes JE, DiMarco JD, Qiu J, Deshpande RP, Gougoutas JZ, Mueller RH. Org. Lett. 2003; 5: 3155
27 Noyori R, Ohkuma T, Kitamura M, Takaya H, Sayo N, Kumobayashi H, Akutagawa S. J. Am. Chem. Soc. 1987; 109: 5856
28 Tschaen DM, Abrahamson L, Cai D, Desmond R, Dolling U.-H, Frey L, Karady S, Shi Y.-J, Verhoeven TR. J. Org. Chem. 1995; 60: 4324
29 Devocelle M, Morteux A, Agbossou F, Dormoy J.-R. Tetrahedron Lett. 1999; 40: 4551
30 Lennon IC, Ramsden JA, Brear CJ, Broady SD, Muir JC. Tetrahedron Lett. 2007; 48: 4623

For reviews see:

31a Dounay AB, Overman LE. Chem. Rev. 2003; 103: 2963
31b Zhou F, Liu Y.-L, Zhou J. Chem. Rev. 2010; 352: 1381
31c Steven A, Overman LE. Angew. Chem. Int. Ed. 2007; 46: 5488
31d Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442

32 Grigg R, Sridharan V, Stevenson P, Worakun T. J. Chem. Soc., Chem. Commun. 1984; 1697
33 Abelman MM, Oh T, Overman LE. J. Org. Chem. 1987; 52: 4133
34 Comins D, Baevsky M, Hong H. J. Am. Chem. Soc. 1992; 114: 10971
35 Grigg R, Sridharan V, Stevenson P, Sukirthalingam S, Worakun T. Tetrahedron 1990; 46: 4003
36 Yoneda R, Sakamoto Y, Oketo Y, Minami K, Harusawa S, Kurihara T. Tetrahedron Lett. 1994; 35: 3749
37 Grigg R, Loganathan V, Santhakumar V, Sridharan V, Teasdale A. Tetrahedron Lett. 1991; 32: 687
38 Nukui S, Sodeoka M, Shibasaki M. Tetrahedron Lett. 1993; 34: 4965

39a Sato Y, Nukui S, Sodeoka M, Shibasaki M. Tetrahedron 1994; 50: 371
39b Nukui S, Sodeoka M, Sasai H, Shibasaki M. J. Org. Chem. 1995; 60: 398

40 Kiewel K, Tallant M, Sulikowski GA. Tetrahedron Lett. 2001; 42: 6621
41 Endo A, Yanagisawa A, Abe M, Tohma S, Kan T, Fukuyama T. J. Am. Chem. Soc. 2002; 124: 6552
42 Kawagishi F, Toma T, Inui T, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2013; 135: 13684
43 Vallin KS. A, Zhang Q, Larhed M, Curran DP, Hallberg A. J. Org. Chem. 2003; 68: 6639
44 Tsukano C, Zhao L, Takemoto Y, Hirama M. Eur. J. Org. Chem. 2010; 4198
45 Ding R, Sung B.-F, Lin G.-Q. Org. Lett. 2012; 14: 4446

For reviews on RCM in total synthesis see:

46a Fürstner A. Angew. Chem. Int. Ed. 2000; 39: 3012
46b Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
46c Connon SJ, Blechert SA. H. Angew. Chem. Int. Ed. 2003; 42: 1900
46d Schrock RE, Hoveyda AH. Angew. Chem. Int. Ed. 2003; 42: 4592
46e Grubbs RH. Tetrahedron 2004; 60: 7117
46f Schrodi Y, Pederson RL. Aldrichimica Acta 2007; 40: 45

47a Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Rutjes FP. J. T. Org. Lett. 2001; 3: 2045
47b Arisawa M, Terada Y, Nakagawa M, Nishida A. Angew. Chem. Int. Ed. 2002; 41: 4732
47c Chen Y, Zhang H, Nan F. J. Comb. Chem. 2004; 6: 684
47d Manzoni L, Colombo M, Scolastico C. Tetrahedron Lett. 2004; 45: 2623
47e Benasar ML, Roca T, Monerris M, Garcia-Diaz D. J. Org. Chem. 2006; 71: 7028

48a Toumi M, Couty F, Evano G. J. Org. Chem. 2008; 73: 1270

For a review see:

48b Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054

49 Hoye TR, Jeffrey CS, Tannakoon MA, Wang J, Zhao H. J. Am. Chem. Soc. 2004; 126: 10210
50 Katz JD, Overman LE. Tetrahedron 2004; 60: 9559

51a Madin A, O’Donnell CJ, Oh T, Old DW, Overman LE, Sharp MJ. Angew. Chem. Int. Ed. 1999; 38: 2934
51b Earley WG, Jacobsen JE, Madin A, Meier GP, O’Donnell CJ, Oh T, Old DW, Overman LE, Sharp MJ. J. Am. Chem. Soc. 2005; 127: 18046

52a Padwa A, Danca MD. Org. Lett. 2002; 4: 715
52b Padwa A, Danca MD, Hardcastle KI, McClure MS. J. Org. Chem. 2003; 68: 929

53 Ahmad VU, Iqbal S. Phytochemistry 1993; 3: 735

54a Nilson MG, Funk RL. Org. Lett. 2006; 8: 3833
54b Nilson MG, Funk RL. Org. Lett. 2010; 12: 4912

55a Deng H, Yang X, Tong Z, Li Z, Zhai H. Org. Lett. 2008; 10: 1791
55b Cheng B, Wu F, Yang X, Zhou Y, Wan X, Zhai H. Chem. Eur. J. 2011; 17: 12569

56 Movassaghi M, Siegel DS, Han S. Chem. Sci. 2010; 1: 561
57 Reyes JC. P, Romo D. Angew. Chem. Int. Ed. 2012; 51: 6870
58 Zöllinger M, Mayer P, Lindel T. J. Org. Chem. 2006; 71: 9431

59a Witherup KM, Ransom RW, Graham AC, Bernard AM, Salvatore MJ, Lumma WC, Anderson PS, Pitzenberger SM, Varga SL. J. Am. Chem. Soc. 1995; 117: 6682
59b Xia Y, Yang Z.-Y, Xia P, Bastow KF, Tachibana Y, Kuo S.-C, Hamel E, Hackl T, Lee K.-H. J. Med. Chem. 1998; 41: 1155
59c Di Fabio R, Tranquillini E, Bertani B, Alvaro G, Micheli F, Sabbatini F, Domenica Pizzi M, Pentassuglia G, Pasquarello A, Messeri T, Donati D, Ratti E, Arban R, Dal Forno G, Reggiani A, Barnaby RJ. Bioorg. Med. Chem. Lett. 2003; 13: 3863
59d Guinó M, Phua PH, Caille J.-C, Hii KK. J. Org. Chem. 2007; 72: 6290

60a Povarov LS, Mikhailov BM. Izv. Akad. Nauk. SSSR, Ser. Khim. 1963; 953
60b Povarov LS. Russ. Chem. Rev. 1967; 36: 656

For reviews, see:

61a Glushkov VA, Tolstikov AG. Russ. Chem. Rev. 2008; 77: 137
61b Kouznetsov VV. Tetrahedron 2009; 65: 2721
61c Masson G, Lalli C, Benohoud M, Dagousset G. Chem. Soc. Rev. 2013; 42: 902
61d Fochi M, Caruana L, Bernardi L. Synthesis 2014; 46: 135

62a Hadden M, Stevenson PJ. Tetrahedron Lett. 1999; 40: 1215
62b Hadden M, Nieuwenhuyzen M, Potts D, Stevenson PJ, Thompson N. Tetrahedron 2001; 57: 5615
62c Hadden M, Nieuwenhuyzen M, Osborne D, Stevenson PJ, Thompson N. Tetrahedron Lett. 2001; 42: 6417
62d Hadden M, Nieuwenhuyzen M, Osborne D, Stevenson PJ, Thompson N, Walker AD. Tetrahedron 2006; 62: 3977

63a Batey AR, Simoncic DP, Lin D, Smyj PR, Lough JA. Chem. Commun. 1999; 651
63b Batey RA, Powell DA. Chem. Commun. 2001; 2362

64 Dagousset G, Retailleau P, Masson G, Zhu J. Chem. Eur. J. 2012; 18: 5869
65 Xia C, Heng L, Ma D. Tetrahedron Lett. 2002; 43: 9405
66 Powell DA, Batey RA. Org. Lett. 2002; 4: 2913
67 Xu AH, Zuend SJ, Woll MG, Tao Y, Jacobsen EN. Science (Washington, D.C.) 2010; 327: 986

68a Liu H, Dagousset G, Masson G, Retailleau P, Zhu J. J. Am. Chem. Soc. 2009; 131: 4598
68b Dagousset G, Zhu J, Masson G. J. Am. Chem. Soc. 2011; 133: 14804

69 Movassaghi M, Hunt DK, Tjandra M. J. Am. Chem. Soc. 2006; 128: 8126
70 Omura S, Murata M, Imamura N, Iwai Y, Tanaka H, Furusaki A, Matsumoto T. J. Antibiot. 1984; 37: 1324
71 Bach T, Schröder J. Liebigs Ann./Recl. 1997; 2265

72a de Faria AR, Matos CR. R, Correia CR. D. Tetrahedron Lett. 1993; 34: 37
72b Correia CR. D, de Faria AR, Carvahlo ES. Tetrahedron Lett. 1995; 36: 5109
72c de Faria AR, Salvador EL, Correia CR. D. J. Org. Chem. 2002; 67: 3651
72d Ambrosio JC. L, Santos RH. de A, Correia CR. D. J. Braz. Chem. Soc. 2003; 14: 27

73a Geissman TA, Waiss Jr AC. J. Org. Chem. 1962; 27: 139
73b Buchanan JG, Jigajinni VB, Singh G, Wightman RH. J. Chem. Soc., Perkin Trans. 1 1987; 2377

74 Gross U, Nieger M, Bräse S. Org. Lett. 2009; 11: 4740

75a Feltenberger JB, Hayashi R, Tang Y, Babiash ES. C, Hsung RP. Org. Lett. 2009; 11: 3666
75b Ma Z.-X, Feltenberger JB, Hsung RP. Org. Lett. 2012; 14: 2742

76a Csuk R, von Scholz Y. Tetrahedron 1994; 50: 10431
76b Lee MG, Du JF, Chun MW, Chu CK. J. Org. Chem. 1997; 62: 1991

77 Song Z, Lu T, Hsung RP, Al-Rashid Z, Ko C, Tang Y. Angew. Chem. Int. Ed. 2007; 46: 4069
78 De Simone F, Gertsch J, Waser J. Angew. Chem. Int. Ed. 2010; 49: 5767
79 Wenkert E, Hudlicky T. J. Org. Chem. 1988; 53: 1953

80a The Chemistry of Heterocyclic Compounds . Vol. 25. Taylor EC, Saxton JE. Wiley-Interscience; New York: 1983: 1994
80b Sundberg RJ. In Indoles. Academic Press; New York: 1996

81a Greshock TJ, Funk RL. J. Am. Chem. Soc. 2006; 128: 4946
81b Huntley RJ, Funk RL. Org. Lett. 2006; 8: 3403

82a Greshock TJ, Funk RL. Org. Lett. 2006; 8: 2643
82b Huntley RL, Funk RL. Org. Lett. 2006; 8: 4775

83 Overman LE. J. Am. Chem. Soc. 1974; 96: 597

84a Imaoka T, Iwamoto O, Noguchi K, Nagasawa K. Angew. Chem. Int. Ed. 2009; 48: 3799
84b Imaoka T, Akimoto T, Iwamoto O, Nagasawa K. Chem. Asian J. 2010; 5: 1810

85 Harrison TJ, Patrick BO, Dake GR. Org. Lett. 2007; 9: 367
86 Kozak JA, Dake GR. Angew. Chem. Int. Ed. 2008; 47: 4221

87a Ishibashi H, Kato I, Takeda Y, Tamura O. Tetrahedron Lett. 2001; 42: 931
87b Kato I, Higashimoto M, Tamura O, Ishibashi H. J. Org. Chem. 2003; 68: 7983

88 Taniguchi T, Iwasaki K, Uchiyama M, Tamura O, Ishibashi H. Org. Lett. 2005; 7: 4389
89 Valencia E, Freyer AJ, Shamma M, Fajardo V. Tetrahedron Lett. 1984; 25: 599
90 Taniguchi T, Tanabe G, Muraoka O, Ishibashi H. Org. Lett. 2008; 10: 197
91 Kuehne MK, Bornmann WG, Parsons WH, Spitzer TD, Blount JF, Zubieta J. J. Org. Chem. 1988; 53: 3439

92a Pouységu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
92b Roche SP, Porco JA. Angew. Chem. Int. Ed. 2011; 50: 4068
92c Silva LF, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
92d Quideau S, Pouységu L, Duffieux D. Synlett 2008; 467

93 Honda T, Shigehisa H. Org. Lett. 2006; 8: 657
94 Shigehisa H, Takayama J, Honda T. Tetrahedron Lett. 2006; 47: 7301
95 Huang X, Shao N, Palani A, Aslanian R, Buevich A. Org. Lett. 2007; 9: 2597

96a Chavan SP, Subbarao YT. Tetrahedron Lett. 1999; 40: 5073
96b Norton Matos MR. P, Afonso CA. M, Batey RA. Tetrahedron Lett. 2001; 42: 7007

97 Le Corre L, Kizirian J.-C, Levraud C, Boucher J.-L, Bonnet V, Dhimane H. Org. Biomol. Chem. 2008; 6: 3388
98 Li Q, Li G, Ma S, Feng P, Shi Y. Org. Lett. 2013; 15: 2601
99 Ren W, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2014; 53: 1818
100 Okano K, Tokuyama H, Fukuyama T. J. Am. Chem. Soc. 2006; 128: 7136