Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones

Gary H. Posner; Leah L. Frye; Martin Hulce

doi:10.1016/S0040-4020(01)82425-X

Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones

Gary H. Posner, Leah L. Frye, Martin Hulce

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

62 Scopus citations

Abstract

Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2 proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7. Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7. Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfnyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.

Original language	English (US)
Pages (from-to)	1401-1407
Number of pages	7
Journal	Tetrahedron
Volume	40
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4020(01)82425-X
State	Published - 1984
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones",

abstract = "Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2 proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7. Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7. Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfnyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.",

author = "Posner, {Gary H.} and Frye, {Leah L.} and Martin Hulce",

year = "1984",

doi = "10.1016/S0040-4020(01)82425-X",

language = "English (US)",

volume = "40",

pages = "1401--1407",

journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones

AU - Posner, Gary H.

AU - Frye, Leah L.

AU - Hulce, Martin

PY - 1984

Y1 - 1984

N2 - Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2 proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7. Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7. Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfnyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.

AB - Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2 proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7. Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7. Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfnyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.

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