33.1.5.2 Alk-1-enyl Sulfoxides, Sulfimides, and Related Compounds (Update 2018)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods for preparation of alk-1-enyl sulfoxides and sulfimides. It focuses on methods published since 2004.

Key words

sulfoxides - sulfimides - vinyl compounds - sulfinylation - Heck reaction - kinetic resolution - asymmetric synthesis - oxidation

• 1 Signore G, Samaritani S, Malanga C, Menicagli R. Synthesis 2006; 762

• 2 Signore G, Calderisi M, Malanga C, Menicagli R. Tetrahedron 2007; 63: 177

• 3 Lenstra DC, Vedovato V, Flegeau EF, Maydom J, Willis MC. Org. Lett. 2016; 18: 2086

• 4 Li YH, Cheng K, Lu XX, Sun JA. Adv. Synth. Catal. 2010; 352: 1876

• 5 Taneda H, Inamoto K, Kondo Y. Chem. Commun. (Cambridge) 2014; 50: 6523

• 6 Alfaro R, Yuste F, Ortiz B, Sánchez-Obregón R, García Ruano JL. Tetrahedron 2009; 65: 357

• 7 Midura WH, Ewas AMM, Mikolajczyk M. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 535

• 8 Moncalves M, Zanotto GM, Toldo JM, Rampon DS, Schneider PH, Goncalves PFB, Rodembusch FS, Silveira CC. RSC Adv. 2017; 7: 8832

• 9 Kimura T, Kobayashi G, Ijima S, Saito S, Imafuji A, Satoh T. Heteroat. Chem. 2017; 28: e21395

• 10 Aversa MC, Barattucci A, Bonaccorsi P, Faggi C, Papalia T. J. Org. Chem. 2007; 72: 4486

• 11 Barattucci A, Di Gioia ML, Leggio A, Minuti L, Papalia T, Siciliano C, Temperini A, Bonaccorsi P. Eur. J. Org. Chem. 2014; 2099

• 12 Aversa MC, Barattucci A, Bonaccorsi P, Temperini A. Eur. J. Org. Chem. 2011; 5668

• 13 Xue QC, Mao ZJ, Shi Y, Mao HB, Cheng YX, Zhu CJ. Tetrahedron Lett. 2012; 53: 1851

• 14 Zhang YX, Wong ZR, Wu XX, Lauw SJL, Huang X, Webster RD, Chi YGR. Chem. Commun. (Cambridge) 2017; 53: 184

• 15 Marino JP, Cao GF. Tetrahedron Lett. 2006; 47: 7711

• 16 Kimura T, Hagiwara M, Nakata T. Tetrahedron Lett. 2007; 48: 9171

• 17 Fernández de la Pradilla R, Lwoff N. Tetrahedron Lett. 2008; 49: 4167

• 18 Simal C, Bates RH, Ureña M, Giménez I, Koutsou C, Infantes L, Fernández de la Pradilla R, Viso A. J. Org. Chem. 2015; 80: 7674

• 19 Sklute G, Marek I. J. Am. Chem. Soc. 2006; 128: 4642

• 20 Fopp C, Romain E, Isaac K, Chemla F, Ferreira F, Jackowski O, Oestreich M, Perez-Luna A. Org. Lett. 2016; 18: 2054

• 21 de Gonzalo G, Torres Pazmiño DE, Ottolina G, Fraaije MW, Carrea G. Tetrahedron: Asymmetry 2006; 17: 130

• 22 Liao SH, Coric I, Wang QG, List B. J. Am. Chem. Soc. 2012; 134: 10 765

• 23 Tang J, Yao PF, Xu XL, Li HY, Huang FP, Nie QQ, Luo MY, Yu Q, Bian HD. RSC Adv. 2016; 6: 44 154

• 24 Bhadra S, Akakura M, Yamamoto H. J. Am. Chem. Soc. 2015; 137: 15 612

• 25 Liu SL, Li XH, Shi TH, Yang GC, Wang HL, Gong JF, Song MP. Eur. J. Org. Chem. 2017; 2280

• 26 Padilha G, Kaufman TS, Silveira CC. Tetrahedron Lett. 2016; 57: 3349

• 27 Tabrizian E, Amoozadeh A, Rahmani S. RSC Adv. 2016; 6: 21 854

• 28 Ghorbani-Choghamarani A, Tahmasbi B, Arghand F, Faryadi S. RSC Adv. 2015; 5: 92 174

• 29 Otokesh S, Kolvari E, Amoozadeh A, Koukabi N. RSC Adv. 2015; 5: 53 749

• 30 Namyslo JC, Stanitzek C. Synthesis 2006; 3367

• 31 Gogoi P, Kalita M, Bhattacharjee T, Barman P. Tetrahedron Lett. 2014; 55: 1028

• 32 Gogoi SR, Boruah JJ, Sengupta G, Saikia G, Ahmed K, Bania KK, Islam NS. Catal. Sci. Technol. 2015; 5: 595

• 33 Maleki B, Hemmati S, Sedrpoushan A, Ashrafi SS, Veisi H. RSC Adv. 2014; 4: 40 505

• 34 Jafarpour M, Ghahramaninezhad M, Rezaeifard A. RSC Adv. 2014; 4: 1601

• 35 Romanelli GP, Vázquez PG, Tundo P. Synlett 2005; 75

• 36 Kamata K, Hirano T, Mizuno N. Chem. Commun. (Cambridge) 2009; 3958

• 37 Boruah JJ, Das SP, Ankireddy SR, Gogoi SR, Islam NS. Green Chem. 2013; 15: 2944

• 38 Reddy KR, Rajasekhar CV, Ravindra A. Synth. Commun. 2006; 36: 3761

• 39 Trivedi R, Lalitha P. Synth. Commun. 2006; 36: 3777

• 40 Wu XF. Tetrahedron Lett. 2012; 53: 4328

• 41 Das SP, Boruah JJ, Chetry H, Islam NS. Tetrahedron Lett. 2012; 53: 1163

• 42 Rezaeifard A, Jafarpour M, Naeimi A, Haddad R. Green Chem. 2012; 14: 3386

• 43 Iwasaki M, Fujii T, Nakajima K, Nishihara Y. Angew. Chem. Int. Ed. 2014; 53: 13 880

• 44 Iwasaki M, Fujii T, Yamamoto A, Nakajima K, Nishihara Y. Chem.–Asian J. 2014; 9: 58

• 45 Pena J, Talavera G, Waldecker B, Alcarazo M. Chem.–Eur. J. 2017; 23: 75

• 46 Iwasaki M, Topolovcan N, Hu H, Nishimura Y, Gagnot G, Nakorn RN, Yuvacharaskul R, Nakajima K, Nishihara Y. Org. Lett. 2016; 18: 1642

• 47 Mlostoń G, Urbaniak K, Linden A, Heimgartner H. Tetrahedron 2009; 65: 8191

• 48 Yang ZH, Yang SY, Haroone MS, He W, Xu JX. Tetrahedron 2017; 73: 3338

• 49 Paradies J. Synthesis 2010; 947

• 50 Kissane M, Lawrence SE, Maguire AR. Tetrahedron: Asymmetry 2010; 21: 871

• 51 Shim YS, Hwang HS, Nam G, Choi KI. Bull. Korean Chem. Soc. 2013; 34: 2317

• 52 Pearson WH, Kropf JE, Choy AL, Lee IY, Kampf JW. J. Org. Chem. 2007; 72: 4135

• 53 Surineni N, Buragohain P, Saikia B, Barua NC, Baruah RK. Tetrahedron Lett. 2015; 56: 6965

• 54 Viso A, Fernández de la Pradilla R, Ureña M, Bates RH, del Águila MA, Colomer I. J. Org. Chem. 2012; 77: 525

• 55 Battace A, Zair T, Doucet H, Santelli M. Synthesis 2006; 3495

• 56 Alberico D, Rudolph A, Lautens M. J. Org. Chem. 2007; 72: 775

• 57 Sokolenko LV, Yagupolskii YL, Vlasenko YG, Babichenko LN, Lipetskij VO, Anselmi E, Magnier E. Tetrahedron Lett. 2015; 56: 1259

• 58 Bachmann DG, Wittwer CC, Gillingham DG. Adv. Synth. Catal. 2013; 355: 3703

• 59 Marino JP, Kieler KA, Kim MW. Tetrahedron 2011; 67: 837

• 60 Mancha G, Cuenca AB, Rodríguez N, Medio-Simón M, Asensio G. Tetrahedron 2010; 66: 6901

• 61 Foucoin F, Caupène C, Lohier J.-F, Santos J, Perrio S, Metzner P. Synthesis 2007; 1315

• 62 He GK, Zhou C, Fu CL, Ma SM. Tetrahedron 2007; 63: 3800

• 63 Fang Z, Zhou C, Fu CL, Ma SM. Org. Biomol. Chem. 2010; 8: 4554

• 64 Lao JR, Fernández-Pérez H, Vidal-Ferran A. Org. Lett. 2015; 17: 4114

• 65 Sokolenko LV, Maletina II, Yagupolskii LM, Yagupolskii YL. Synlett 2010; 2075

• 66 Brebion F, Goddard JP, Fensterbank L, Malacria M. Org. Lett. 2008; 10: 1917

• 67 Ochiai M, Naito M, Miyamoto K, Hayashi W, Nakanishi W. Chem.–Eur. J. 2010; 16: 8713

• 68 Bizet V, Buglioni L, Bolm C. Angew. Chem. Int. Ed. 2014; 53: 5639

• 69 Collet F, Dodd RH, Dauban P. Org. Lett. 2008; 10: 5473