The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

Shlomo Levinger; Ranjeet Nair; Alfred Hassner

doi:10.3762/bjoc.4.32

The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

Shlomo Levinger
, Ranjeet Nair
, Alfred Hassner

Department of Chemistry

Bar-Ilan University

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

3 Scopus citations

Abstract

The impact of a remote aromatic nucleus on the stereochemical outcome of the conjugate addition of α-sulfonylallylic carbanions to an α,β-unsaturated ester was investigated. α-Regioselectivity coupled with anti-diastereoselectivity is accompanied by a prominent preference for relative configuration 3 over 4. The 9-anthryl moiety has shown itself greatly superior over all other groups in this bias. A lithium ion-aromatic π interaction has been postulated as decisive for the remote transmission of chirality.

Original language	English
Article number	32
Journal	Beilstein Journal of Organic Chemistry
Volume	4
DOIs	https://doi.org/10.3762/bjoc.4.32
State	Published - 23 Sep 2008

Keywords

Cation-π interaction
Conjugate addition
Diastereoselectivity
Regioselectivity
Remote chiral induction

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10.3762/bjoc.4.32

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title = "The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate",

abstract = "The impact of a remote aromatic nucleus on the stereochemical outcome of the conjugate addition of α-sulfonylallylic carbanions to an α,β-unsaturated ester was investigated. α-Regioselectivity coupled with anti-diastereoselectivity is accompanied by a prominent preference for relative configuration 3 over 4. The 9-anthryl moiety has shown itself greatly superior over all other groups in this bias. A lithium ion-aromatic π interaction has been postulated as decisive for the remote transmission of chirality.",

keywords = "Cation-π interaction, Conjugate addition, Diastereoselectivity, Regioselectivity, Remote chiral induction",

author = "Shlomo Levinger and Ranjeet Nair and Alfred Hassner",

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doi = "10.3762/bjoc.4.32",

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AU - Levinger, Shlomo

AU - Nair, Ranjeet

AU - Hassner, Alfred

PY - 2008/9/23

Y1 - 2008/9/23

N2 - The impact of a remote aromatic nucleus on the stereochemical outcome of the conjugate addition of α-sulfonylallylic carbanions to an α,β-unsaturated ester was investigated. α-Regioselectivity coupled with anti-diastereoselectivity is accompanied by a prominent preference for relative configuration 3 over 4. The 9-anthryl moiety has shown itself greatly superior over all other groups in this bias. A lithium ion-aromatic π interaction has been postulated as decisive for the remote transmission of chirality.

AB - The impact of a remote aromatic nucleus on the stereochemical outcome of the conjugate addition of α-sulfonylallylic carbanions to an α,β-unsaturated ester was investigated. α-Regioselectivity coupled with anti-diastereoselectivity is accompanied by a prominent preference for relative configuration 3 over 4. The 9-anthryl moiety has shown itself greatly superior over all other groups in this bias. A lithium ion-aromatic π interaction has been postulated as decisive for the remote transmission of chirality.

KW - Cation-π interaction

KW - Conjugate addition

KW - Diastereoselectivity

KW - Regioselectivity

KW - Remote chiral induction

UR - https://www.scopus.com/pages/publications/80052073543

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SN - 1860-5397

VL - 4

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

M1 - 32

ER -

The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

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Keywords

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