Michael reactions of allylic sulfones with nitroolefins. Regio- and stereochemical control

Eugene Ghera; Efrat Ben-Yaakov; Tamar Yechezkel; Alfred Hassner

doi:10.1016/s0040-4039(00)79071-x

Michael reactions of allylic sulfones with nitroolefins. Regio- and stereochemical control

Eugene Ghera, Efrat Ben-Yaakov, Tamar Yechezkel, Alfred Hassner

Department of Chemistry

Bar-Ilan University

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

10 Scopus citations

Abstract

Michael addition of allylsulfone carbanions to nitroolefins where shown to be sensitive to substitution in both the donor and the acceptor. While sulfone 10 gave predominantly products of γ-addition with aromatic nitroolefins, addition to aliphatic nitroolefins produced almost exclusively α-adducts. In the presence of an OH function in the sulfone (see 13) only (Z) γ-adducts were observed, while a bromine substituent reversed the regiochemistry.

Original language	English
Pages (from-to)	2741-2744
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	19
DOIs	https://doi.org/10.1016/s0040-4039(00)79071-x
State	Published - 5 May 1992

Bibliographical note

Funding Information:
double bond in 15 - 17 in a more selectivem anner than in sulfone 10. This coordinationa ffectsa lso charged istributionl eadingt o greaterp referencef or r-attack.A contrarye ffectc ould be expectedin 14, in which charged elocalizationa t the CH2 terminus,d ue to the participationo f allylic bromine, should enhancea ttacka t the sulfone-substitutecda rbon,l eadingt o 18 - 19,r espectivelyS. tudiesa re continuing for the rationalizationo f the substitutionin fluence,w ith emphasiso n the unprecedentede ffecto f allylic substituentse quallyd istancedf rom the reactivet ermini. This should contributet o the exploitationo f suchr eactionsf or new and selectives yntheticr outes. AcknowledgementS: upport of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged.

Funding Information:
Acknowkdgement: Support of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged.

Funding

double bond in 15 - 17 in a more selectivem anner than in sulfone 10. This coordinationa ffectsa lso charged istributionl eadingt o greaterp referencef or r-attack.A contrarye ffectc ould be expectedin 14, in which charged elocalizationa t the CH2 terminus,d ue to the participationo f allylic bromine, should enhancea ttacka t the sulfone-substitutecda rbon,l eadingt o 18 - 19,r espectivelyS. tudiesa re continuing for the rationalizationo f the substitutionin fluence,w ith emphasiso n the unprecedentede ffecto f allylic substituentse quallyd istancedf rom the reactivet ermini. This should contributet o the exploitationo f suchr eactionsf or new and selectives yntheticr outes. AcknowledgementS: upport of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged. Acknowkdgement: Support of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged.

Funders	Funder number
US-Israel Binational Science Foundationi s gratefullya cknowledged
US-Israel Binational Science Foundationi s gratefullya cknowledged

Keywords

Michael reactions
allylic anions
nitroolefins
sulfones

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10.1016/s0040-4039(00)79071-x

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title = "Michael reactions of allylic sulfones with nitroolefins. Regio- and stereochemical control",

abstract = "Michael addition of allylsulfone carbanions to nitroolefins where shown to be sensitive to substitution in both the donor and the acceptor. While sulfone 10 gave predominantly products of γ-addition with aromatic nitroolefins, addition to aliphatic nitroolefins produced almost exclusively α-adducts. In the presence of an OH function in the sulfone (see 13) only (Z) γ-adducts were observed, while a bromine substituent reversed the regiochemistry.",

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author = "Eugene Ghera and Efrat Ben-Yaakov and Tamar Yechezkel and Alfred Hassner",

note = "Funding Information: double bond in 15 - 17 in a more selectivem anner than in sulfone 10. This coordinationa ffectsa lso charged istributionl eadingt o greaterp referencef or r-attack.A contrarye ffectc ould be expectedin 14, in which charged elocalizationa t the CH2 terminus,d ue to the participationo f allylic bromine, should enhancea ttacka t the sulfone-substitutecda rbon,l eadingt o 18 - 19,r espectivelyS. tudiesa re continuing for the rationalizationo f the substitutionin fluence,w ith emphasiso n the unprecedentede ffecto f allylic substituentse quallyd istancedf rom the reactivet ermini. This should contributet o the exploitationo f suchr eactionsf or new and selectives yntheticr outes. AcknowledgementS: upport of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged. Funding Information: Acknowkdgement: Support of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged.",

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doi = "10.1016/s0040-4039(00)79071-x",

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AU - Ghera, Eugene

AU - Ben-Yaakov, Efrat

AU - Yechezkel, Tamar

AU - Hassner, Alfred

N1 - Funding Information: double bond in 15 - 17 in a more selectivem anner than in sulfone 10. This coordinationa ffectsa lso charged istributionl eadingt o greaterp referencef or r-attack.A contrarye ffectc ould be expectedin 14, in which charged elocalizationa t the CH2 terminus,d ue to the participationo f allylic bromine, should enhancea ttacka t the sulfone-substitutecda rbon,l eadingt o 18 - 19,r espectivelyS. tudiesa re continuing for the rationalizationo f the substitutionin fluence,w ith emphasiso n the unprecedentede ffecto f allylic substituentse quallyd istancedf rom the reactivet ermini. This should contributet o the exploitationo f suchr eactionsf or new and selectives yntheticr outes. AcknowledgementS: upport of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged. Funding Information: Acknowkdgement: Support of this research by a grant from the US-Israel Binational Science Foundationi s gratefullya cknowledged.

PY - 1992/5/5

Y1 - 1992/5/5

N2 - Michael addition of allylsulfone carbanions to nitroolefins where shown to be sensitive to substitution in both the donor and the acceptor. While sulfone 10 gave predominantly products of γ-addition with aromatic nitroolefins, addition to aliphatic nitroolefins produced almost exclusively α-adducts. In the presence of an OH function in the sulfone (see 13) only (Z) γ-adducts were observed, while a bromine substituent reversed the regiochemistry.

AB - Michael addition of allylsulfone carbanions to nitroolefins where shown to be sensitive to substitution in both the donor and the acceptor. While sulfone 10 gave predominantly products of γ-addition with aromatic nitroolefins, addition to aliphatic nitroolefins produced almost exclusively α-adducts. In the presence of an OH function in the sulfone (see 13) only (Z) γ-adducts were observed, while a bromine substituent reversed the regiochemistry.

KW - Michael reactions

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Michael reactions of allylic sulfones with nitroolefins. Regio- and stereochemical control

Abstract

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Keywords

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