Complete Asymmetric Induction in Synthesis of Enantiomerically Pure Steroid Intermediates of Natural Configuration

Gary H. Posner; Martin Hulee; John P. Mallamo; Steven A. Drexler; Jon Clardy

doi:10.1021/jo00338a047

Complete Asymmetric Induction in Synthesis of Enantiomerically Pure Steroid Intermediates of Natural Configuration

Gary H. Posner, Martin Hulee, John P. Mallamo, Steven A. Drexler, Jon Clardy

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

37 Scopus citations

Abstract

Enantiomerically pure steroid intermediates (S)-1 and (S)-(+)-2 of natural absolute configuration have been prepared with complete asymmetric induction during zinc dibromide mediated vinylmagnesium bromide conjugate addition to enantiomerically pure, crystalline, stable cyclopentenone sulfoxide (S)-(+)-5, which has been prepared on a 10-g scale.

Original language	English (US)
Pages (from-to)	5244-5246
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	46
Issue number	25
DOIs	https://doi.org/10.1021/jo00338a047
State	Published - Dec 1981
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00338a047

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title = "Complete Asymmetric Induction in Synthesis of Enantiomerically Pure Steroid Intermediates of Natural Configuration",

abstract = "Enantiomerically pure steroid intermediates (S)-1 and (S)-(+)-2 of natural absolute configuration have been prepared with complete asymmetric induction during zinc dibromide mediated vinylmagnesium bromide conjugate addition to enantiomerically pure, crystalline, stable cyclopentenone sulfoxide (S)-(+)-5, which has been prepared on a 10-g scale.",

author = "Posner, {Gary H.} and Martin Hulee and Mallamo, {John P.} and Drexler, {Steven A.} and Jon Clardy",

year = "1981",

month = dec,

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language = "English (US)",

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AU - Posner, Gary H.

AU - Hulee, Martin

AU - Mallamo, John P.

AU - Drexler, Steven A.

AU - Clardy, Jon

PY - 1981/12

Y1 - 1981/12

N2 - Enantiomerically pure steroid intermediates (S)-1 and (S)-(+)-2 of natural absolute configuration have been prepared with complete asymmetric induction during zinc dibromide mediated vinylmagnesium bromide conjugate addition to enantiomerically pure, crystalline, stable cyclopentenone sulfoxide (S)-(+)-5, which has been prepared on a 10-g scale.

AB - Enantiomerically pure steroid intermediates (S)-1 and (S)-(+)-2 of natural absolute configuration have been prepared with complete asymmetric induction during zinc dibromide mediated vinylmagnesium bromide conjugate addition to enantiomerically pure, crystalline, stable cyclopentenone sulfoxide (S)-(+)-5, which has been prepared on a 10-g scale.

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