Work

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

Year: 2009

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol900456v

Authors: Kay M. Buchner, Timothy B. Clark, Janice M. N. Loy, Thong X. Nguyen, K. A. Woerpel

Institution: University of California, Irvine

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1875460084, Silacyclopropanes: Building Blocks for Organic Synthesis, SILACYCLOPROPANES--BUILDING BLOCKS FOR ORGANIC SYNTHESIS