Organic letters

Cu-Catalyzed Asymmetric Conjugate Additions of Dialkyl-and Diarylzinc Reagents to Acyclic β-Silyl-α, β-unsaturated Ketones. Synthesis of Allylsilanes in High …

MA Kacprzynski, SA Kazane, TL May…

Index: Kacprzynski, Monica A.; Kazane, Stephanie A.; May, Tricia L.; Hoveyda, Amir H. Organic Letters, 2007 , vol. 9, # 16 p. 3187 - 3190

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Citation Number: 38

Abstract

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 β-silyl-α, β-unsaturated ketones. The catalytic asymmetric protocol allows access to versatile allylsilanes that bear a trisubstituted olefin in high diastereo-and enantiomeric purity.