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Alkylidenesilacyclopropanes Derived from Allenes: Applications to the Selective Synthesis of Triols and Homoallylic Alcohols

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journal contribution
posted on 21.05.2009, 00:00 by Kay M. Buchner, Timothy B. Clark, Janice M. N. Loy, Thong X. Nguyen, K. A. Woerpel
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.