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Stereoselective synthesis of vinylsilanes from alkynylsilanes via hydromagnesiation. Application to a synthesis of 7(E)-dodecenyl acetate and dihydrojasmone

1983; Elsevier BV; Volume: 24; Issue: 10 Linguagem: Inglês

10.1016/s0040-4039(00)81598-1

1873-3581

Fumie Sato, Hiroshi Watanabe, Youichi Tanaka, Takafumi Yamaji, Masao Satô,

Chemical Synthesis and Reactions

Abstract Hydromagnesiation of 1-trimethylsilyl-1-alkynes with isobutylmagnesium bromide in the presence of a catalytic amount of Cp 2 TiCl 2 followed by treatment of the resulting vinyl Grignard reagents with alkyl iodides and copper iodide affords (Z)-1,2-dialkylvinylsilanes in excellent yields. The utility of the reaction sequence is illustrated by a simple synthesis of 7(E)-dodecenyl acetate and dihydrojasmone.