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4.4.34.7 Method 7: By Wittig Reaction

DOI: 10.1055/sos-SD-004-00770

Oshima, K.Science of Synthesis, (20024728.

The reaction, in the presence of soluble lithium salts, of nonstabilized ylides at low temperature with aliphatic derivatives of acylsilanes gives moderate to good (3782%) yields of (Z)-1,2-disubstituted vinylsilanes in excellent (>96%) isomeric purities for normal alkyl derivatives.[‌40‌] The Wittig reaction of aldehydes with triphenyl[(trimethylsilyl)methylene]phosphorane (Ph3P=CHSiMe3) does not give a satisfactory result. However, the reaction of triphenyl[3-(trimethylsilyl)allylidene]phosphorane (Ph3P=CHCH=CHSiMe3) with ketones such as acetone, cyclohexanone, and benzophenone affords the corresponding silylated dienes (Scheme 22).[‌41‌]

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