40.1.8 Product Subclass 8: Piperazines

Abstract

The piperazine unit is widely distributed in natural products and life-saving small-molecule pharmaceuticals. It is the third most common nitrogen heterocycle occurring in pharmaceuticals approved by the U. S. Food and Drug Administration. This chapter covers strategies for the synthesis and transformations of piperazines, with both classical methods and recent developments reviewed. A major focus is on cyclization reactions such as intramolecular hydroaminations, multicomponent approaches, and routes from ethane-1,2-diamine substrates. Also discussed are approaches based on hydrogenation of (hydro)pyrazines by heterogeneous catalysis and by (asymmetric) homogeneous catalysis. Finally, a variety of transformations involving modification of a substituent on a piperazine ring are surveyed, including arylations, alkylations, and oxidations.

Key words

piperazines - cyclization - hydroamination - Ugi reaction - allylation - arylation - hydrogenation - dearomatization - asymmetric synthesis - lithiation - activation of C-H bonds - cross-coupling reactions

• 1 The Merck Index, 11th Ed.. Budavari S. Merck&Co.; Rahway, NJ 1989: 7431

• 2 Pietsch J, Sacher F, Schmidt W, Brauch H.-J. Water Res. 2001; 35: 3537

• 3 Paoletti P, Ciampolini M, Vacca A. J. Phys. Chem. 1963; 67: 1065

• 4 Meuresch M, Westhues S, Leitner W, Klankermayer J. Angew. Chem. Int. Ed. 2016; 55: 1392

• 5 Krueger PJ, Jan J. Can. J. Chem. 1970; 48: 3236

• 6 Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10 257

• 7 Stegmeier F, Warmuth M, Sellers WR, Dorsch M. Clin. Pharmacol. Ther. 2010; 87: 543

• 8 Fluphenazine. In: Martindale: The Complete Drug Reference 36th ed. Sweetman S. Pharmaceutical Press London 2009; 998

• 9 Lue TF. Engl. J. Med. 2000; 342: 1802

• 10 Vacca JP, Dorsey BD, Schleif WA, Levin RB, McDaniel SL, Darke PL, Zugay J, Quintero JC, Blahy OM, Roth E, Sardana VV, Schlabach AJ, Graham PI, Condra JH, Gotlib L, Holloway MK, Lin J, Chen I.-W, Vastag K, Ostovic D, Anderson PS, Emini EA, Huff JR. Proc. Natl. Acad. Sci. U. S. A. 1994; 91: 4096

• 11 Shapiro DA, Renock S, Arrington E, Chiodo LA, Liu L.-X, Sibley DR, Roth BL, Mailman R. Neuropsychopharmacology 2003; 28: 1400

• 12 Burka JM, Bower KS, Vanroekel RC, Stutzman RD, Kuzmowych CP, Howard RS. Am. J. Ophthalmol. 2005; 140: 83

• 13 Di Fabio R, Griffante C, Alvaro G, Pentassuglia G, Pizzi DA, Donati D, Rossi T, Guercio G, Mattioli M, Cimarosti Z, Marchioro C, Provera S, Zonzini L, Montanari D, Melotto S, Gerrard PA, Trist DG, Ratti E, Corsi M. J. Med. Chem. 2009; 52: 3238

• 14 Kane J, Honigfeld G, Singer J, Meltzer H. Arch. Gen. Psychiatry 1988; 45: 789

• 15 Koch RW, Dessy RE. J. Org. Chem. 1982; 47: 4452

• 16 Shono T, Kise N, Shirakawa E, Matsumoto H, Okazaki E. J. Org. Chem. 1991; 56: 3063

• 17 Mercer GJ, Sigman MS. Org. Lett. 2003; 5: 1591

• 18 Vairaprakash P, Periasamy M. J. Org. Chem. 2006; 71: 3636

• 19 Aboussafy CL, Clive DLJ. J. Org. Chem. 2012; 77: 5125

• 20 Peng J, Clive DLJ. J. Org. Chem. 2009; 74: 513

• 21 Kitchen LJ, Pollard CB. J. Am. Chem. Soc. 1947; 69: 854

• 22 Olsen CA, Christensen C, Nielsen B, Farah MM, Witt M, Clausen RP, Kristensen JL, Franzyk H, Jaroszewski JW. Org. Lett. 2006; 8: 3371

• 23 Ottesen LK, Olsen CA, Witt M, Jaroszewski JW, Franzyk H. Chem.–Eur. J. 2009; 15: 2966

• 24 Zhai H, Borzenko A, Lau YY, Ahn SH, Schafer LL. Angew. Chem. Int. Ed. 2012; 51: 12 219

• 25 James T, Simpson I, Grant JA, Sridharan V, Nelson A. Org. Lett. 2013; 15: 6094

• 26 Yao L.-F, Wang Y, Huang K.-W. Org. Chem. Front. 2015; 2: 721

• 27 Yamamoto K, Yoshikawa Y, Ohue M, Inuki S, Ohno H, Oishi S. Org. Lett. 2019; 21: 373

• 28 Cochran BM, Michael FE. Org. Lett. 2008; 10: 329

• 29 Lu Z, Stahl SS. Org. Lett. 2012; 14: 1234

• 30 Ferber B, Prestat G, Vogel S, Madec D, Poli G. Synlett 2006; 2133

• 31 Nakhla JS, Schultz DM, Wolfe JP. Tetrahedron 2009; 65: 6549

• 32 Ye K.-Y, Cheng Q, Zhuo C.-X, Dai L.-X, You S.-L. Angew. Chem. Int. Ed. 2016; 55: 8113

• 33 Zhuo C.-X, Zhang X, You S.-L. ACS Catal. 2016; 6: 5307

• 34 Sullivan HB, Day AR. J. Org. Chem. 1964; 29: 326

• 35 Mickelson JW, Belonga KL, Jacobsen EJ. J. Org. Chem. 1995; 60: 4177

• 36 Ashton KS, Denti M, Norman MH, Jean Jr DJSt. Tetrahedron Lett. 2014; 55: 4501

• 37 Fischer E. Chem. Ber. 1906; 39: 2893

• 38 Van Brabandt W, Vanwalleghem M, D’hooghe M, De Kimpe N. J. Org. Chem. 2006; 71: 7083

• 39 Guitot K, Carboni S, Reiser O, Piarulli U. J. Org. Chem. 2009; 74: 8433

• 40 Chamakuri S, Jain P, Guduru SKR, Arney JW, MacKenzie KR, Santini C, Young DW. J. Org. Chem. 2018; 83: 6541

• 41 Schanen V, Cherrier M.-P, de Melo SJ, Quiriona J.-C, Husson H.-P. Synthesis 1996; 833

• 42 O’Reilly MC, Lindsley CW. Org. Lett. 2012; 14: 2910

• 43 Guduru SKR, Chamakuri S, Raji IO, MacKenzie KR, Santini C, Young DW. J. Org. Chem. 2018; 83: 11 777

• 44 Dar’in D, Bakulina O, Chizhova M, Krasavin M. Org. Lett. 2015; 17: 3930

• 45 Usmanova L, Dar’in D, Novikov MS, Gureev M, Krasavin M. J. Org. Chem. 2018; 83: 5859

• 46 Luescher MU, Vo C.-VT, Bode JW. Org. Lett. 2014; 16: 1236

• 47 Siau W.-Y, Bode JW. J. Am. Chem. Soc. 2014; 136: 17 726

• 48 Luescher MU, Bode JW. Angew. Chem. Int. Ed. 2015; 54: 10 884

• 49 Hsieh S.-Y, Bode JW. Org. Lett. 2016; 18: 2098

• 50 Chen Z, Wu J, Chen Y, Li L, Xia Y, Li Y, Liu W, Lei T, Yang L, Gao D, Li W. Organometallics 2012; 31: 6005

• 51 Suárez-Pantiga S, Colas K, Johansson MJ, Mendoza A. Angew. Chem. Int. Ed. 2015; 54: 14 094

• 52 Roh J, Karabanovich G, Novakova V, Šimůnek T, Vávrová K. Synthesis 2016; 48: 4580

• 53 Henry DW. J. Heterocycl. Chem. 1966; 3: 503

• 54 Mishani E, Dence CS, McCarthy TJ, Welch MJ. Tetrahedron Lett. 1996; 37: 319

• 55 Liu KG, Robichaud AJ. Tetrahedron Lett. 2005; 46: 7921

• 56 Huang J, Xu W, Xie H, Li S. J. Org. Chem. 2012; 77: 7506

• 57 Jida M, Laconde G, Soueidan O.-M, Lebegue N, Revelant G, Pelinski L, Agbossou-Niedercorn F, Deprez B, Deprez-Poulain R. Tetrahedron Lett. 2012; 53: 5215

• 58 Maity P, König B. Org. Lett. 2008; 10: 1473

• 59 Yahiro N, Ito S. Bull. Chem. Soc. Jpn. 1986; 59: 321

• 60 Tsuji Y, Huh K.-T, Ohsugi Y, Watanabe Y. J. Org. Chem. 1985; 50: 1365

• 61 Dömling A, Huang Y. Synthesis 2010; 2859

• 62 Nenajdenko VG, Reznichenko AL, Balenkova ES. Tetrahedron 2007; 63: 3031

• 63 Dick CR. J. Org. Chem. 1967; 32: 72

• 64 Trinchera P, Musio B, Degennaro L, Moliterni A, Falcicchio A, Luisi R. Org. Biomol. Chem. 2012; 10: 1962

• 65 Takehiro Y, Hirotaki K, Takeshita C, Furuno H, Hanamoto T. Tetrahedron 2013; 69: 7448

• 66 Trost BM, Osipov M, Dong G. J. Am. Chem. Soc. 2010; 132: 15800

• 67 Crestey F, Witt M, Jaroszewski JW, Franzyk H. J. Org. Chem. 2009; 74: 5652

• 68 Das BK, Pradhan S, Punniyamurthy T. Org. Lett. 2018; 20: 4444

• 69 Hili R, Rai V, Yudin AK. J. Am. Chem. Soc. 2010; 132: 2889

• 70 Heine NB, Kaldas SJ, Belding L, Shmatova O, Dudding T, Nenajdenko VG, Studer A, Yudin AK. J. Org. Chem. 2016; 81: 5209

• 71 Manna SK, Panda G. RSC Adv. 2013; 3: 18 332

• 72 Kour H, Paul S, Singh PP, Gupta M, Gupta R. Tetrahedron Lett. 2013; 54: 761

• 73 Yar M, McGarrigle EM, Aggarwal VK. Angew. Chem. Int. Ed. 2008; 47: 3784

• 74 Matlock JV, Svejstrup TD, Songara P, Overington S, McGarrigle EM, Aggarwal VK. Org. Lett. 2015; 17: 5044

• 75 Yar M, McGarrigle EM, Aggarwal VK. Org. Lett. 2009; 11: 257

• 76 Bagnoli L, Scarponi C, Rossi MG, Testaferri L, Tiecco M. Chem.–Eur. J. 2011; 17: 993

• 77 Lu C, Lu X. Org. Lett. 2002; 4: 4677

• 78 Ye Z, Adhikari S, Xia Y, Dai M. Nat. Commun. 2018; 9: 721

• 79 Fukudome Y, Naito H, Hata T, Urabe H. J. Am. Chem. Soc. 2008; 130: 1820

• 80 Borlinghaus N, Gergel S, Nestl BM. ACS Catal. 2018; 8: 3727

• 81 Raw SA, Wilfred CD, Taylor RJK. Chem. Commun. (Cambridge) 2003; 2286

• 82 Raw SA, Wilfred CD, Taylor RJK. Org. Biomol. Chem. 2004; 2: 788

• 83 Fan L, Chen W, Qian C. Tetrahedron Lett. 2013; 54: 231

• 84 Nordstrøm LU, Madsen R. Chem. Commun. (Cambridge) 2007; 5034

• 85 Lorentz-Petersen LLR, Nordstrøm LU, Madsen R. Eur. J. Org. Chem. 2012; 6752

• 86 Montgomery TD, Rawal VH. Org. Lett. 2016; 18: 740

• 87 Mouhtaram M, Jung L, Stambach JF. Tetrahedron 1993; 49: 1391

• 88 Jang JI, Kang SY, Kang KH, Park YS. Tetrahedron 2011; 67: 6221

• 89 Rossen K, Sager J, DiMichele LM. Tetrahedron Lett. 1997; 38: 3183

• 90 Matsumoto S, Ishii M, Kimura K, Ogura K. Bull. Chem. Soc. Jpn. 2004; 77: 1897

• 91 Powell NA, Ciske FL, Clay EC, Cody WL, Downing DM, Blazecka PG, Holsworth DD, Edmunds JJ. Org. Lett. 2004; 6: 4069

• 92 Vidal-Albalat A, Rodríguez S, Gonzaëlez FV. Org. Lett. 2014; 16: 1752

• 93 Meninno S, Vidal-Albalat A, Lattanzi A. Org. Lett. 2015; 17: 4348

• 94 Balsells J, DiMichele L, Liu J, Kubryk M, Hansen K, Armstrong JD. Org. Lett. 2005; 7: 1039

• 95 Uozumi Y, Tanahashi A, Hayashi T. J. Org. Chem. 1993; 58: 6826

• 96 Rychnovsky SD, Beauchamp T, Vaidyanathan R, Kwan T. J. Org. Chem. 1998; 63: 6363

• 97 Chauhan N, Pradhan S, Ghorai MK. J. Org. Chem. 2019; 84: 1757

• 98 Xia P.-J, Sun Y.-H, Xiao J.-A, Zhou Z.-F, Wen S.-S, Xiong Y, Ou G.-C, Chen X.-Q, Yang H. J. Org. Chem. 2015; 80: 11 573

• 99 Ruider SA, Müller S, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 11 908

• 100 Piper JR, Rose LM, Johnston TP. J. Org. Chem. 1972; 37: 4476

• 101 Rossen K, Weissman SA, Sager J, Reamer RA, Askin D, Volante RP, Reider PJ. Tetrahedron Lett. 1995; 36: 6419

• 102 Rossen K, Pye PJ, DiMichele LM, Volante RP, Reider PJ. Tetrahedron Lett. 1998; 39: 6823

• 103 Kuwano R, Ito Y. J. Org. Chem. 1999; 64: 1232

• 104 Pye PJ, Rossen K, Reamer RA, Tsou NN, Volante RP, Reider PJ. J. Am. Chem. Soc. 1997; 119: 6207

• 105 Wang Y, Liu Y, Li K, Yang G, Zhang W. Adv. Synth. Catal. 2017; 359: 1933

• 106 Li Y, He Y, Chen F, Fan Q. Chin. J. Chem. 2014; 32: 991

• 107 Leclerc J.-P, Fagnou K. Angew. Chem. Int. Ed. 2006; 45: 7781

• 108 Lunn G. J. Org. Chem. 1987; 52: 1043

• 109 He Y.-M, Song F.-T, Fan Q.-H. Top. Curr. Chem. 2013; 343: 145

• 110 Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557

• 111 Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357

• 112 Glorius F. Org. Biomol. Chem. 2005; 3: 4171

• 113 Tang W, Zhang X. Chem. Rev. 2003; 103: 3029

• 114 Fuchs R. EP 803 502, 1997

• 115 Huang W.-X, Liu L.-J, Wu B, Feng G.-S, Wang B, Zhou Y.-G. Org. Lett. 2016; 18: 3082

• 116 Hu S.-B, Zhai X.-Y, Shen H.-Q, Zhou Y.-G. Adv. Synth. Catal. 2018; 360: 1334

• 117 Higashida K, Nagae H, Mashima K. Adv. Synth. Catal. 2016; 358: 3949

• 118 Lyle RE, Thomas JJ. J. Org. Chem. 1965; 30: 1907

• 119 Miyake FY, Yakushijin K, Horne DA. Org. Lett. 2000; 2: 3185

• 120 Andersson H, Banchelin TS.-L, Das S, Gustafsson M, Olsson R, Almqvist F. Org. Lett. 2010; 12: 284

• 121 Campos KR. Chem. Soc. Rev. 2007; 36: 1069

• 122 Berkheij M, van der Sluis L, Sewing C, den Boer DJ, Terpstra JW, Hiemstra H, Iwema Bakker WI, van den Hoogenband A, van Maarseveen JH. Tetrahedron Lett. 2005; 46: 2369

• 123 Robinson SP, Sheikh NS, Baxter CA, Coldham I. Tetrahedron Lett. 2010; 51: 3642

• 124 Bennie LS, Kerr WJ, Middleditch M, Watson AJB. Chem. Commun. (Cambridge) 2011; 47: 2264

• 125 Barker G, O’Brien P, Campos KR. Org. Lett. 2010; 12: 4176

• 126 McDermott BP, Campbell AD, Ertan A. Synlett 2008; 875

• 127 Gelardi G, Barker G, O’Brien P, Blakemore DC. Org. Lett. 2013; 15: 5424

• 128 Firth JD, O’Brien P, Ferris L. J. Am. Chem. Soc. 2016; 138: 651

• 129 Li C.-J. Acc. Chem. Res. 2009; 42: 335

• 130 Doye S. Angew. Chem. Int. Ed. 2001; 40: 3351

• 131 Murahashi S.-I. Angew. Chem. Int. Ed. Engl. 1995; 34: 2443

• 132 Ishii Y, Chatani N, Kakiuchi F, Murai S. Organometallics 1997; 16: 3615

• 133 Greßies S, Klauck FJR, Kim JH, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2018; 57: 9950

• 134 Payne PR, Garcia P, Eisenberger P, Yim JC.-H, Schafer LL. Org. Lett. 2013; 15: 2182

• 135 Prier CK, Rankic DA, MacMillan DWC. Chem. Rev. 2013; 113: 5322

• 136 Tucker JW, Stephenson CRJ. J. Org. Chem. 2012; 77: 1617

• 137 Narayanam JMR, Stephenson CRJ. Chem. Soc. Rev. 2011; 40: 102

• 138 Hu J, Wang J, Nguyen TH, Zheng N. Beilstein J. Org. Chem. 2013; 9: 1977

• 139 McNally A, Prier CK, MacMillan DWC. Science (Washington, D. C.) 2011; 334: 1114

• 140 Miyake Y, Nakajima K, Nishibayashi Y. J. Am. Chem. Soc. 2012; 134: 3338

• 141 Prier CK, MacMillan DWC. Chem. Sci. 2014; 5: 4173

• 142 Noble A, MacMillan DWC. J. Am. Chem. Soc. 2014; 136: 11 602

• 143 Williams L, Booth SE, Undheim K. Tetrahedron 1994; 50: 13 697

• 144 Xu G.-Q, Xu J.-T, Feng Z.-T, Liang H, Wang Z.-Y, Qin Y, Xu P.-F. Angew. Chem. Int. Ed. 2018; 57: 5110

• 145 Genovino J, Lütz S, Sames D, Toureë BB. J. Am. Chem. Soc. 2013; 135: 12 346

• 146 Nyberg K, Servin R. Acta Chem. Scand., Ser. B 1976; 30: 640

• 147 Vedejs E, Jure M. Angew. Chem. Int. Ed. 2005; 44: 3974

• 148 Kagan HB, Fiaud JC. Top. Stereochem. 1988; 18: 249

• 149 Keith JM, Larrow JF, Jacobsen EN. Adv. Synth. Catal. 2001; 343: 5

• 150 Binanzer M, Hsieh S.-Y, Bode JW. J. Am. Chem. Soc. 2011; 133: 19 698

• 151 Kreituss I, Bode JW. Nature Chem. 2017; 9: 446

• 152 Bartoli G, Todesco PE. Acc. Chem. Res. 1977; 10: 125

• 153 Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443

• 154 Pelletier JC, Chengalvala M, Cottom J, Feingold I, Garrick L, Green D, Hauze D, Huselton C, Jetter J, Kao W, Kopf GS, Lundquist IV JT, Mann C, Mehlmann J, Rogers J, Shanno L, Wrobel J. Bioorg. Med. Chem. 2008; 16: 6617

• 155 Iwama S, Kitano T, Fukuya F, Honda Y, Sato Y, Notake M, Morie T. Bioorg. Med. Chem. Lett. 2004; 14: 2567

• 156 Tangallapally RP, Yendapally R, Lee RE, Lenaerts AJM, Lee RE. J. Med. Chem. 2005; 48: 8261

• 157 Otsuka M, Endo K, Shibata T. Chem. Commun. (Cambridge) 2010; 46: 336

• 158 Meng X, Cai Z, Xiao S, Zhou W. J. Fluorine Chem. 2013; 146: 70

• 159 Bolliger JL, Frech CM. Tetrahedron 2009; 65: 1180

• 160 Lin Y, Li M, Ji X, Wu J, Cao S. Tetrahedron 2017; 73: 1466

• 161 Johnson CR, Ansari MI, Coop A. ACS Omega 2018; 3: 10 886

• 162 Xu G, Wang Y.-G. Org. Lett. 2004; 6: 985

• 163 Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12 564

• 164 Muci AR, Buchwald SL. Top. Curr. Chem. 2002; 219: 131

• 165 Park NH, Vinogradova EV, Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2015; 54: 8259

• 166 Hartwig JF. Acc. Chem. Res. 2008; 41: 1534

• 167 Castillo M, Forns P, Erra M, Mir M, López M, Maldonado M, Orellana A, Carreño C, Ramis I, Miralpeix M, Vidal B. Bioorg. Med. Chem. Lett. 2012; 22: 5419

• 168 Kügler F, Ermert J, Kaufholz P, Coenen HH. Molecules 2015; 20: 470

• 169 Wolfe JP, Wagaw S, Buchwald SL. J. Am. Chem. Soc. 1996; 118: 7215

• 170 Cawley MJ, Geoffrey F, Cloke N, Fitzmaurice RJ, Pearson SE, Scott JS, Caddick S. Org. Biomol. Chem. 2008; 6: 2820

• 171 Urgaonkar S, Verkade JG. Adv. Synth. Catal. 2004; 346: 611

• 172 Reddy NP, Tanaka M. Tetrahedron Lett. 1997; 38: 4807

• 173 Hoi KH, Çalimsiz S, Froese RDJ, Hopkinson AC, Organ MG. Chem.–Eur. J. 2011; 17: 3086

• 174 Reilly SW, Mach RH. Org. Lett. 2016; 18: 5272

• 175 Brenner E, Schneider R, Fort Y. Tetrahedron Lett. 2000; 41: 2881

• 176 Desmarets C, Schneider R, Fort Y. J. Org. Chem. 2002; 67: 3029

• 177 Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400

• 178 Ma D, Cai Q. Acc. Chem. Res. 2008; 41: 1450

• 179 Kunz K, Lui N, In: Copper-Mediated Cross-Coupling Reactions Evano E, Blanchard N. John Wiley & Sons Hoboken, NJ 2013; 725 744

• 180 Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16 136

• 181 Yong F.-F, Teo Y.-C, Tan K.-N. Tetrahedron Lett. 2013; 54: 5332

• 182 Yong F.-F, Teo Y.-C. Synlett 2010; 3068

• 183 Buchwald SL, Klapars A, Antilla JC, Job GE, Wolter M, Kwong FY, Nordmann G, Hennessy EJ. WO 02 085 838, 2002

• 184 Quadri M, Papke RL, Horenstein NA. Bioorg. Med. Chem. 2016; 24: 286

• 185 de Lange B, Lambers-Verstappen MH, Schmieder-van de Vondervoort L, Sereinig N, de Rijk R, de Vries AHM, de Vries JG. Synlett 2006; 3105

• 186 Bhunia S, Kumar SV, Ma D. J. Org. Chem. 2017; 82: 12 603

• 187 Sandtorv AH, Stuart DR. Angew. Chem. Int. Ed. 2016; 55: 15 812

• 188 Purkait N, Kervefors G, Linde E, Olofsson B. Angew. Chem. Int. Ed. 2018; 57: 11 427

• 189 Hepperle M, Eckert J, Gala D. Tetrahedron Lett. 1999; 40: 5655

• 190 Gonela UM, Ablordeppey SY. New J. Chem. 2019; 43: 2861

• 191 Keesara S. Tetrahedron Lett. 2015; 56: 6685

• 192 ten Hoeve W, Kruse CG, Luteyn JM, Thiecke JRG, Wynberg H. J. Org. Chem. 1993; 58: 5101

• 193 Gao K, Yorimitsu H, Osuka A. Eur. J. Org. Chem. 2015; 2678

• 194 Shimasaki T, Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2010; 49: 2929

• 195 Mesganaw T, Silberstein AL, Ramgren SD, Nathel NFF, Hong X, Liu P, Garg NK. Chem. Sci. 2011; 2: 1766

• 196 Hie L, Ramgren SD, Mesganaw T, Garg NK. Org. Lett. 2012; 14: 4182

• 197 Wiensch EM, Montgomery J. Angew. Chem. Int. Ed. 2018; 57: 11 045

• 198 Korch KM, Eidamshaus C, Behenna DC, Nam S, Horne D, Stoltz BM. Angew. Chem. Int. Ed. 2015; 54: 179

• 199 Sun AW, Hess SN, Stoltz BM. Chem. Sci. 2019; 10: 788

• 200 Jin S, Wessig P, Liebscher J. J. Org. Chem. 2001; 66: 3984

• 201 Ross SD, Finkelstein M. J. Am. Chem. Soc. 1963; 85: 2603

• 202 Wang H.-J, Earley WG, Lewis RM, Srivastava RR, Zych AJ, Jenkins DM, Fairfax DJ. Tetrahedron Lett. 2007; 48: 3043

• 203 Gladstone SG, Earley WG, Acker JK, Martin GS. Tetrahedron Lett. 2009; 50: 3813

• 204 Wang H.-J, Wang Y, Csakai AJ, Earley WG, Herr RJ. J. Comb. Chem. 2009; 11: 355

• 205 Zhu Q, Yuan Q, Chen M, Guo M, Huang H. Angew. Chem. Int. Ed. 2017; 56: 5101

• 206 Zhu Q, Yang P, Chen M, Hu J, Yang L. Synthesis 2018; 50: 2587

• 207 Min G, Seo J, Ko HM. J. Org. Chem. 2018; 83: 8417

• 208 Bugaenko DI, Yurovskaya MA, Karchava AV. J. Org. Chem. 2017; 82: 2136

• 209 Dong H.-R, Chen Z.-B, Li R.-S, Dong H.-S, Xie Z.-X. RSC Adv. 2015; 5: 10768

• 210 Bugaenko DI, Yurovskaya MA, Karchava AV. Org. Lett. 2018; 20: 6389

• 211 Yavari I, Bayat MJ, Ghazanfarpour-Darjani M. Tetrahedron Lett. 2014; 55: 5595