Asymmetric epoxidation of nearly symmetrical cis-alkenes. Sharpless epoxidation of (1,2-dialkyl)vinylsilanols
1997; Elsevier BV; Volume: 38; Issue: 1 Linguagem: Inglês
10.1016/s0040-4039(96)02226-5
ISSN1873-3581
AutoresL.H. Li, Dongliang Wang, Tak Hang Chan,
Tópico(s)Chemical Synthesis and Reactions
Resumo(1,2-Dialkyl)vinylalkoxysilanes 3 were hydrolyzed in the presence of catalysts (CuClLiCl or NiBr2) to give the corresponding silanols 2 in high yield. Sharpless epoxidation of 2 followed by protodesilylation gave optically active epoxides 7. The overall approach can be considered as asymmetric epoxidation of nearly symmetrical simple cis-alkenes and has been applied to the synthesis of (+)-disparlure.
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