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Diastereoselective Synthesis of Chiral (E)-Vinylsilanes
S. Perrone, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
24 April 2007 (online)
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.