Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides

Gary H. Posner; John P. Mallamo; Kyo Miura; Martin Hulce

doi:10.1351/pac198153122307

Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides

Gary H. Posner, John P. Mallamo, Kyo Miura, Martin Hulce

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Abstract

A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.

Original language	English (US)
Pages (from-to)	2307-2314
Number of pages	8
Journal	Pure and Applied Chemistry
Volume	53
Issue number	12
DOIs	https://doi.org/10.1351/pac198153122307
State	Published - Jan 1 1981
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)

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title = "Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides",

abstract = "A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.",

author = "Posner, {Gary H.} and Mallamo, {John P.} and Kyo Miura and Martin Hulce",

note = "Funding Information: from the National Science Foundation (CHE 79-15161), from the Donors of the Petroleum Research Fund, administered by the Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "1981",

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doi = "10.1351/pac198153122307",

language = "English (US)",

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AU - Posner, Gary H.

AU - Mallamo, John P.

AU - Miura, Kyo

AU - Hulce, Martin

N1 - Funding Information: from the National Science Foundation (CHE 79-15161), from the Donors of the Petroleum Research Fund, administered by the Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 1981/1/1

Y1 - 1981/1/1

N2 - A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.

AB - A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.

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Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides

Abstract

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