Recent Progress of Transition-Metal-Catalyzed Enantioselective Hydroalkynylation of Alkenes

Abstract

Catalytic asymmetric hydroalkynylation of unsaturated alkenes provides a straightforward method to construct stereocenters substituted by an alkynyl group. Here we provide an overview of the recent progress of catalytic asymmetric hydroalkynylation reactions. Our recent development of an iridium-catalyzed enantioselective hydroalkynylation of enamides is also discussed.

1 Introduction

2 Catalytic Asymmetric Hydroalkynylation of Electron-Deficient Alkenes

3 Catalytic Asymmetric Hydroalkynylation of Electron-Neutral Alkenes

4 Catalytic Asymmetric Hydroalkynylation of Electron-Rich Alkenes

5 Conclusion

Key words

alkynes - hydroalkynylation - asymmetric catalysis - iridium - enamide

• References

• 1a Stang PJ, Diederich F. Modern Acetylene Chemistry . VCH; Weinheim: 1995
• 1b Diederich F, Stang PJ, Tykwinski RR. Acetylene Chemistry . Wiley-VCH; Weinheim: 2005
• 1c Trost BM, Li C.-J. Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations. Wiley; New York: 2014
• 1d Schobert H. Chem. Rev. 2014; 114: 1743
• 1e Trotuş I.-T, Zimmermann T, Schüth F. Chem. Rev. 2014; 114: 1761
• 1f Chinchilla R, Nájera C. Chem. Rev. 2014; 114: 1783
• 2a Tan L, Chen C.-Y, Tillyer RD, Grabowski EJ. J, Reider PJ. Angew. Chem. Int. Ed. 1999; 38: 711
• 2b Knöpfel TF, Boyall D, Carreira EM. Org. Lett. 2004; 6: 2281
• 2c Zhou Y, Wang R, Xu Z, Yan W, Liu L, Kang Y, Han Z. Org. Lett. 2004; 6: 4147
• 2d Yamashita M, Yamada K.-I, Tomioka K. Org. Lett. 2005; 7: 2369
• 2e Blay G, Fernández I, Marco-Aleixandre A, Pedro JR. J. Org. Chem. 2006; 71: 6674
• 2f Blay G, Cardona L, Climent E, Pedro JR. Angew. Chem. 2008; 120: 5675
• 2g Blay G, Cardona L, Fernandez I, Marco-Aleixandre A, Munoz MC, Pedro JR. Org. Biomol. Chem. 2009; 7: 4301
• 2h Cui S, Walker SD, Woo JC. S, Borths CJ, Mukherjee H, Chen MJ, Faul MM. J. Am. Chem. Soc. 2010; 132: 436
• 2i Blay G, Cardona L, Pedro JR, Sanz-Marco A. Chem. Eur. J. 2012; 18: 12966
• 2j Blay G, Ceballos E, Monleón A, Pedro JR. Tetrahedron 2012; 68: 2128
• 2k Blay G, Brines A, Monleón A, Pedro JR. Chem. Eur. J. 2012; 18: 2440
• 3a Kwak Y.-S, Corey EJ. Org. Lett. 2004; 6: 3385
• 3b Larionov OV, Corey EJ. Org. Lett. 2010; 12: 300
• 4 Cozzi PG, Alesi S. Chem. Commun. 2004; 2448
• 5 Teruaki M, Keisuke S, Kenso S, Toshio S. Chem. Lett. 1979; 8: 447
• 6a Chong JM, Shen L, Taylor NJ. J. Am. Chem. Soc. 2000; 122: 1822
• 6b Wu TR, Chong JM. J. Am. Chem. Soc. 2005; 127: 3244
• 7 Nishimura T, Tokuji S, Sawano T, Hayashi T. Org. Lett. 2009; 11: 3222
• 8 Shinji FF. K. T, Pablo Z, Takashi I, Dean BM. C. E. Bull. Chem. Soc. Jpn. 2007; 80: 1635

For hydroalkynylation of carbonyls and imines, see:
• 9a Zani L, Bolm C. Chem. Commun. 2006; 4263
• 9b Trost BM, Weiss AH. Adv. Synth. Catal. 2009; 351: 963
• 9c Liu J, Dasgupta S, Watson MP. Beilstein J. Org. Chem. 2015; 11: 2696
• 10a Knöpfel TF, Zarotti P, Ichikawa T, Carreira EM. J. Am. Chem. Soc. 2005; 127: 9682

For a racemic version, see:
• 10b Knöpfel TF, Carreira EM. J. Am. Chem. Soc. 2003; 125: 6054
• 11 Sanz-Marco A, Garcia-Ortiz A, Blay G, Pedro JR. Chem. Commun. 2014; 50: 2275
• 12a Nishimura T, Guo X.-X, Uchiyama N, Katoh T, Hayashi T. J. Am. Chem. Soc. 2008; 130: 1576

For racemic versions, see:
• 12b Nikishin GI, Kovalev IP. Tetrahedron Lett. 1990; 31: 7063
• 12c Lerum RV, Chisholm JD. Tetrahedron Lett. 2004; 45: 6591
• 12d Zhou L, Chen L, Skouta R, Jiang H.-F, Li C.-J. Org. Biomol. Chem. 2008; 6: 2969
• 12e Villarino L, Garcia-Fandino R, Lopez F, Mascarenas JL. Org. Lett. 2012; 14: 2996
• 13 Nishimura T, Sawano T, Hayashi T. Angew. Chem. Int. Ed. 2009; 48: 8057
• 14 Fillion E, Zorzitto AK. J. Am. Chem. Soc. 2009; 131: 14608
• 15 Nishimura T, Sawano T, Ou K, Hayashi T. Chem. Commun. 2011; 47: 10142
• 16 Ito J.-I, Fujii K, Nishiyama H. Chem. Eur. J. 2013; 19: 601
• 17a Yazaki R, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 10275
• 17b Yazaki R, Kumagai N, Shibasaki M. Chem. Asian J. 2011; 6: 1778
• 18 Sawano T, Ashouri A, Nishimura T, Hayashi T. J. Am. Chem. Soc. 2012; 134: 18936
• 19a Shirakura M, Suginome M. Angew. Chem. Int. Ed. 2010; 49: 3827

For a racemic version, see:
• 19b Shirakura M, Suginome M. J. Am. Chem. Soc. 2008; 130: 5410
• 20 Gatineau D, Giordano L, Buono G. J. Am. Chem. Soc. 2011; 133: 10728
• 21 Fan B.-M, Yang Q.-J, Hu J, Fan C.-L, Li S.-F, Yu L, Huang C, Tsang WW, Kwong FY. Angew. Chem. Int. Ed. 2012; 51: 7821
• 22 Sawano T, Ou K, Nishimura T, Hayashi T. Chem. Commun. 2012; 48: 6106
• 23 Fan B, Xu J, Yang Q, Li S, Chen H, Liu S, Yu L, Zhou Y, Wang L. Org. Lett. 2013; 15: 5956
• 24a Hu J, Yang Q, Xu J, Huang C, Fan B, Wang J, Lin C, Bian Z, Chan AS. C. Org. Biomol. Chem. 2013; 11: 814
• 24b Yang Q, Choy PY, Fan B, Kwong FY. Adv. Synth. Catal. 2015; 357: 2345
• 25 Wang M.-X. Chem. Commun. 2015; 51: 6039
• 26 Jiang L, Job GE, Klapars A, Buchwald SL. Org. Lett. 2003; 5: 3667
• 27 Gooßen LJ, Salih KS. M, Blanchot M. Angew. Chem. Int. Ed. 2008; 47: 8492
• 28a Pan S, Ryu N, Shibata T. J. Am. Chem. Soc. 2012; 134: 17474
• 28b Shibata T, Tsuchikama K, Pan S. J. Synth. Org. Chem. Jpn. 2013; 71: 1182
• 28c Crisenza GE. M, Sokolova OO, Bower JF. Angew. Chem. Int. Ed. 2015; 54: 14866
• 29 Bai X.-Y, Wang Z.-X, Li B.-J. Angew. Chem. Int. Ed. 2016; 55: 9007
• 30 Ding C.-H, Hou X.-L. Chem. Rev. 2011; 111: 1914