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

Autor: Buchner KM; Department of Chemistry, University of California, Irvine, California 92697-2025, USA., Clark TB, Loy JM, Nguyen TX, Woerpel KA
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2009 May 21; Vol. 11 (10), pp. 2173-5.
DOI: 10.1021/ol900456v
Abstrakt: 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.
Databáze: MEDLINE