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

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

doi:10.1021/ol900456v

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	2173-2175
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	10
DOIs	https://doi.org/10.1021/ol900456v
State	Published - May 21 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "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.",

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T2 - Applications to the selective synthesis of triols and homoallylic alcohols

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AU - Clark, Timothy B.

AU - Loy, Janice M.N.

AU - Nguyen, Thong X.

AU - Woerpel, K. A.

PY - 2009/5/21

Y1 - 2009/5/21

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AB - 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.

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