Concepedia

Copper‐Catalyzed Addition of Nucleophilic Silicon to Aldehydes

Virginie Cirriez, Corentin Rasson, Thomas Hermant, Julien Pétrignet, Koen Robeyns, Olivier Riant

Angewandte Chemie International Edition · 2013 · 86 citations · 45 references

DOI

Concepts

Abstract

How to train your silane: A new family of chiral copper(I) complexes that bear a bifluoride counteranion were prepared and used in the first example of the enantioselective transfer of a silyl group to an aldehyde. This procedure provides fast access to non-racemic α-hydroxysilanes in high enantioselectivities.

References

45

Enantioselective Conjugate Silyl Additions to Cyclic and Acyclic Unsaturated Carbonyls Catalyzed by Cu Complexes of Chiral N-Heterocyclic Carbenes

Kang-Sang Lee, Amir H. Hoveyda · Journal of the American Chemical Society · 2010 · 300 citations · Full text

Silylboranes as New Tools in Organic Synthesis

Toshimichi Ohmura, Michinori Suginome · Bulletin of the Chemical Society of Japan · 2009 · 272 citations · Full text

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Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles

Eduard Hartmann, Devendra J. Vyas, Martin Oestreich · Chemical Communications · 2011 · 214 citations

, , +16

Convenient Preparation of Silylboranes

Michinori Suginome, Takanori Matsuda, Yoshihiko Ito · Organometallics · 2000 · 193 citations

, , +11

Metal-Free Catalytic C–Si Bond Formation in an Aqueous Medium. Enantioselective NHC-Catalyzed Silyl Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls

Jeannette M. O’Brien, Amir H. Hoveyda · Journal of the American Chemical Society · 2011 · 168 citations