Vinylcyclopropane oxygenation. Anti diastereoselectivity through an unexpected transition-state geometry

Ken S. Feldman; Carolyn M. Kraebel

Vinylcyclopropane oxygenation. Anti diastereoselectivity through an unexpected transition-state geometry

Ken S. Feldman, Carolyn M. Kraebel

Chemistry

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

30 Scopus citations

Abstract

Ester-substituted vinylcyclopropanes react with molecular oxygen via a radical-mediated [3-atom + 2-atom] addition to form 1,2-dioxolanes with predominantly anti stereochemistry. The degree of anti stereoselectivity can be controlled by the electronic nature of the radical stabilizing substituent R.

Original language	English (US)
Pages (from-to)	4574-4576
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	57
Issue number	17
State	Published - 1992

All Science Journal Classification (ASJC) codes

Organic Chemistry

Cite this

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title = "Vinylcyclopropane oxygenation. Anti diastereoselectivity through an unexpected transition-state geometry",

abstract = "Ester-substituted vinylcyclopropanes react with molecular oxygen via a radical-mediated [3-atom + 2-atom] addition to form 1,2-dioxolanes with predominantly anti stereochemistry. The degree of anti stereoselectivity can be controlled by the electronic nature of the radical stabilizing substituent R.",

author = "Feldman, {Ken S.} and Kraebel, {Carolyn M.}",

year = "1992",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Vinylcyclopropane oxygenation. Anti diastereoselectivity through an unexpected transition-state geometry

AU - Feldman, Ken S.

AU - Kraebel, Carolyn M.

PY - 1992

Y1 - 1992

N2 - Ester-substituted vinylcyclopropanes react with molecular oxygen via a radical-mediated [3-atom + 2-atom] addition to form 1,2-dioxolanes with predominantly anti stereochemistry. The degree of anti stereoselectivity can be controlled by the electronic nature of the radical stabilizing substituent R.

AB - Ester-substituted vinylcyclopropanes react with molecular oxygen via a radical-mediated [3-atom + 2-atom] addition to form 1,2-dioxolanes with predominantly anti stereochemistry. The degree of anti stereoselectivity can be controlled by the electronic nature of the radical stabilizing substituent R.

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M3 - Article

AN - SCOPUS:0001459770

SN - 0022-3263

VL - 57

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EP - 4576

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Vinylcyclopropane oxygenation. Anti diastereoselectivity through an unexpected transition-state geometry

Abstract

All Science Journal Classification (ASJC) codes

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