4.8 Article

Cu-catalyzed asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic β-silyl-α,β-unsaturated ketones.: Synthesis of allylsilanes in high diastereo- and enantiomeric purity

Journal

ORGANIC LETTERS
Volume 9, Issue 16, Pages 3187-3190

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol071331k

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Funding

  1. NIGMS NIH HHS [GM-47480] Funding Source: Medline

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[GRAPHICS] A readily available and simple (MW = 444.5 g/mol) valine-based chiral phosphine is used to promote highly efficient catalytic asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic beta-silyl-alpha,beta-unsaturated ketones. The catalytic asymmetric protocol allows access to versatile allylsilanes that bear a trisubstituted olefin in high diastereo- and enantiomeric purity.

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