Alkylidenesilacyclopropanes derived from allenes: applications to the selective synthesis of triols and homoallylic alcohols.

ABSTRACT: Several alkylidenesilacyclopropanes were prepared by silver-mediated silylene transfer to allenes. Oxasilacyclopentanes derived from allenes were prepared with high regio- and diastereoselectivity by a two-step, one-flask silacyclopropanation/carbonyl insertion reaction. Triols and homoallylic alcohols were formed diastereoselectively by functionalizing the oxasilacyclopentanes. An optically active allene (>98% ee) was utilized to synthesize an enantiopure homoallylic alcohol in 96% ee.

SUBMITTER: Buchner KM 

PROVIDER: S-EPMC2705192 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature