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Synfacts 2007(5): 0513-0513  
DOI: 10.1055/s-2007-968447
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Chiral (E)-Vinylsilanes

Contributor(s): Mark Lautens, Frédéric Ménard
S. Perrone, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The area of asymmetric allylic subsitution (AAS) has been the subject of intense activity for many years. The authors reported an interesting approach where the chirality of an allylsilane is transposed to the distal position of a vinylsilane product. The AAS takes place regioselectively in an SN2′ fashion with pentafluorobenzoate as the nucleofuge. The versatility of the resulting vinylsilanes was demonstrated by their derivatization to the corresponding enones 9, or to a vinylboronic ester 10.