‘True’ Chirality Transfer from Silicon to Carbon

doi:10.1055/s-2005-869915

Synfacts 2005(0): 0039-0039
DOI: 10.1055/s-2005-869915

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

‘True’ Chirality Transfer from Silicon to Carbon

Contributor(s): Hisashi Yamamoto, Matthew Boxer

M. Oestreich*, S. Rendler
Albert-Ludwigs Universität, Freiburg, Germany
‘‘True’’ Chirality Transfer from Silicon to Carbon: Asymmetric Amplification in a Reagent-Controlled Palladium-Catalyzed Hydrosilylation
Angew. Chem. Int. Ed. 2005, 44: 1661-1664

Abstract

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Key words

chirality transfer - asymmetric amplification - hydrosilation

Significance

Palladium-catalyzed hydrosilation giving perfect stereoselectivity has been accomplished. A chirality transfer from silicon to carbon resulting in asymmetric amplification and highly optical pure products is the result. A positive non-linear effect has implied a matched mismatched scenario involved in the proposed mechanism.

Comment

‘True’ chirality transfer from silicon to carbon has long been an elusive transformation in chemistry. Not only does this paper describe this transformation giving high ee’s, but also their protocol involves a somewhat rare case of asymmetric amplification. The origin of this very interesting asymmetric amplification still awaits further investigation.

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