Synlett 2015; 26(17): 2332-2335
DOI: 10.1055/s-0034-1378789
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© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Hydrosilylation of 1,1-Disubstituted Alkenes

Jianhui Chen
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang, 310027, P. R. of China   Email: luzhan@zju.edu.cn
,
Minyi Cao
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang, 310027, P. R. of China   Email: luzhan@zju.edu.cn
,
Biao Cheng
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang, 310027, P. R. of China   Email: luzhan@zju.edu.cn
,
Zhan Lu*
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang, 310027, P. R. of China   Email: luzhan@zju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 17 May 2015

Accepted after revision: 16 June 2015

Publication Date:
23 July 2015 (online)

Abstract

Catalytic asymmetric hydrosilylation of 1,1-disubstituted alkenes has been summarized. The intramolecular reactions proceed efficiently in the presence of noble transition-metal rhodium. The highly enantioselective intermolecular processes are catalyzed by earth-abundant transition-metal iron.

 
  • References

    • 1a Chan TH, Wang D. Chem. Rev. 1992; 92: 995
    • 1b Bains W, Tacke R. Curr. Opin. Drug Discovery Dev. 2003; 6: 526
    • 1c Pooni PK, Showell GA. Mini-Rev. Med. Chem. 2006; 6: 1169
    • 1d Gately S, West R. Drug Dev. Res. 2007; 68: 156
    • 1e Franz AK, Wilson SO. J. Med. Chem. 2013; 56: 388
    • 1f Min GK, Hernández D, Skrydstrup T. Acc. Chem. Res. 2013; 46: 457

      For a review on palladium-catalyzed asymmetric hydrosilylation of alkenes, see:
    • 3a Gibson SE, Rudd M. Adv. Synth. Catal. 2007; 349: 781

    • For some samples on palladium-catalyzed hydrosilylation of alkenes, see:
    • 3b Uozumi Y, Hayashi T. J. Am. Chem. Soc. 1991; 113: 9887
    • 3c Kitayama K, Uozumi Y, Hayashi T. J. Chem. Soc., Chem. Commun. 1995; 1533
    • 3d Weber I, Jones GB. Tetrahedron Lett. 2001; 42: 6983
    • 3e Jensen JF, Svendsen BY, la Cour TV, Pedersen HL, Johannsen M. J. Am. Chem. Soc. 2002; 124: 4558
    • 3f Guo X, Xie J, Hou G, Shi W, Wang L, Zhou Q. Tetrahedron: Asymmetry 2004; 15: 2231
    • 3g Rendler S, Fröhlich R, Keller M, Oestreich M. Eur. J. Org. Chem. 2008; 2582
    • 3h Zhang F, Fan Q. Org. Biomol. Chem. 2009; 7: 4470
    • 3i Junge K, Wendt B, Enthaler S, Beller M. ChemCatChem 2010; 2: 453

    • For a review on rhodium-catalyzed asymmetric hydrosilylation of alkenes, see:
    • 3j Ito J.-i, Nishiyama H. Top. Organomet. Chem. 2011; 37: 185
  • 4 Thomas SP, Aggarwal VK. Angew. Chem. Int. Ed. 2009; 48: 1896
  • 5 Yamamoto K, Hayashi T, Zembayashi M, Kumada M. J. Organomet. Chem. 1976; 118: 161
  • 6 Yamamoto K, Hayashi T, Uramoto Y, Ito R, Kumada M. J. Organomet. Chem. 1976; 118: 331
  • 7 Tamao K, Tohma T, Inui N, Nakayama O, Ito Y. Tetrahedron Lett. 1990; 31: 7333
  • 8 Tamao K, Nakamura K, Ishii H, Yamaguchi S, Shiro M. J. Am. Chem. Soc. 1996; 118: 12469
  • 9 Bergens SH, Noheda P, Whelan J, Bosnich B. J. Am. Chem. Soc. 1992; 114: 2121
    • 10a Wang X, Bosnich B. Organometallics 1994; 13: 4131
    • 10b Bosnich B. Acc. Chem. Res. 1998; 31: 667
  • 11 Fu P.-F, Brard L, Li Y, Marks TJ. J. Am. Chem. Soc. 1995; 117: 7157
    • 12a Gountchev TI, Tilley TD. Organometallics 1999; 18: 5661
    • 12b Buch F, Harder S. Z. Naturforsch., B: J. Chem. Sci. 2008; 63: 169
    • 13a Haque MB, Roberts BP. Tetrahedron Lett. 1996; 37: 9123
    • 13b Haque MB, Roberts BP, Tocher DA. J. Chem. Soc., Perkin Trans. 1 1998; 2881
    • 13c Cai Y, Roberts BP, Tocher DA. J. Chem. Soc., Perkin Trans. 1 2002; 1376
  • 14 Chen J.-H, Cheng B, Cao M.-Y. Angew. Chem. Int. Ed. 2015; 54: 4661