Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions

Laura F. Basil; A. I. Meyers; A. Hassner

doi:10.1016/s0040-4020(01)01151-6

Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions

Laura F. Basil, A. I. Meyers, A. Hassner

Department of Chemistry

Colorado State University

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

10 Scopus citations

Abstract

Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to α,β-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes.

Original language	English
Pages (from-to)	207-213
Number of pages	7
Journal	Tetrahedron
Volume	58
Issue number	2
DOIs	https://doi.org/10.1016/s0040-4020(01)01151-6
State	Published - 7 Jan 2002

Bibliographical note

Funding Information:
Authors (L. B., A. I. M.) are grateful to the National Science Foundation for partial financial support. A. I. M. and A. H. are also grateful to the US–Israel Binational Science Foundation for financial support. Dr Chris Rithner and Susie Miller are gratefully acknowledged for obtaining NOESY, TOCSY NMR and X-ray crystal data, respectively.

Funding

Authors (L. B., A. I. M.) are grateful to the National Science Foundation for partial financial support. A. I. M. and A. H. are also grateful to the US–Israel Binational Science Foundation for financial support. Dr Chris Rithner and Susie Miller are gratefully acknowledged for obtaining NOESY, TOCSY NMR and X-ray crystal data, respectively.

Funders	Funder number
United States-Israel Binational Science Foundation
National Science Foundation

Keywords

Chiral β-substituted carboxylic acids
Michael additions
pK of sulfonylmethylenes and unsaturated oxazolines

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10.1016/s0040-4020(01)01151-6

Cite this

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title = "Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions",

abstract = "Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to α,β-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes.",

keywords = "Chiral β-substituted carboxylic acids, Michael additions, pK of sulfonylmethylenes and unsaturated oxazolines",

author = "Basil, {Laura F.} and Meyers, {A. I.} and A. Hassner",

note = "Funding Information: Authors (L. B., A. I. M.) are grateful to the National Science Foundation for partial financial support. A. I. M. and A. H. are also grateful to the US–Israel Binational Science Foundation for financial support. Dr Chris Rithner and Susie Miller are gratefully acknowledged for obtaining NOESY, TOCSY NMR and X-ray crystal data, respectively. ",

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AU - Meyers, A. I.

AU - Hassner, A.

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AB - Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to α,β-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes.

KW - Chiral β-substituted carboxylic acids

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Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions

Abstract

Bibliographical note

Funding

Keywords

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