Intermolecular [3+2] MIRC reactions with alkynoates. Asymmetric Michael addition leading to a nonracemic cyclopentene-annulated α,β-butenolide

Philippe Nakache; Eugene Ghera; Alfred Hassner

doi:10.1016/S0040-4039(00)00867-4

Intermolecular [3+2] MIRC reactions with alkynoates. Asymmetric Michael addition leading to a nonracemic cyclopentene-annulated α,β-butenolide

Philippe Nakache, Eugene Ghera, Alfred Hassner

Department of Chemistry

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

10 Scopus citations

Abstract

A novel Michael-initiated ring closure reacton involving allylic chlorosulfone (2) and γ-alkoxy-α,β-ynoates to afford 4- methylenecyclopentenecarboxylates is reported, while with γ-alkylynoates no reaction occurred. With chiral phenyl ynoates 4, the reaction proceeds by 1,3-asymmetric induction and leads further to a nonracemic annulated α,β- butenolide (7). (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5583-5587
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4039(00)00867-4
State	Published - 15 Jul 2000

Bibliographical note

Funding Information:
The authors wish to thank the US–Israel Science Foundation and the Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University for financial support, and Dr. Hugo E. Gottlieb for his valuable help in NMR analysis.

Keywords

Asymmetric induction
Butenolides
Cyclopentenecarboxylates
Lithium ion chelation
Michael reactions

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10.1016/S0040-4039(00)00867-4

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title = "Intermolecular [3+2] MIRC reactions with alkynoates. Asymmetric Michael addition leading to a nonracemic cyclopentene-annulated α,β-butenolide",

abstract = "A novel Michael-initiated ring closure reacton involving allylic chlorosulfone (2) and γ-alkoxy-α,β-ynoates to afford 4- methylenecyclopentenecarboxylates is reported, while with γ-alkylynoates no reaction occurred. With chiral phenyl ynoates 4, the reaction proceeds by 1,3-asymmetric induction and leads further to a nonracemic annulated α,β- butenolide (7). (C) 2000 Elsevier Science Ltd.",

keywords = "Asymmetric induction, Butenolides, Cyclopentenecarboxylates, Lithium ion chelation, Michael reactions",

author = "Philippe Nakache and Eugene Ghera and Alfred Hassner",

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AU - Nakache, Philippe

AU - Ghera, Eugene

AU - Hassner, Alfred

N1 - Funding Information: The authors wish to thank the US–Israel Science Foundation and the Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University for financial support, and Dr. Hugo E. Gottlieb for his valuable help in NMR analysis.

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N2 - A novel Michael-initiated ring closure reacton involving allylic chlorosulfone (2) and γ-alkoxy-α,β-ynoates to afford 4- methylenecyclopentenecarboxylates is reported, while with γ-alkylynoates no reaction occurred. With chiral phenyl ynoates 4, the reaction proceeds by 1,3-asymmetric induction and leads further to a nonracemic annulated α,β- butenolide (7). (C) 2000 Elsevier Science Ltd.

AB - A novel Michael-initiated ring closure reacton involving allylic chlorosulfone (2) and γ-alkoxy-α,β-ynoates to afford 4- methylenecyclopentenecarboxylates is reported, while with γ-alkylynoates no reaction occurred. With chiral phenyl ynoates 4, the reaction proceeds by 1,3-asymmetric induction and leads further to a nonracemic annulated α,β- butenolide (7). (C) 2000 Elsevier Science Ltd.

KW - Asymmetric induction

KW - Butenolides

KW - Cyclopentenecarboxylates

KW - Lithium ion chelation

KW - Michael reactions

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JO - Tetrahedron Letters

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Intermolecular [3+2] MIRC reactions with alkynoates. Asymmetric Michael addition leading to a nonracemic cyclopentene-annulated α,β-butenolide

Abstract

Bibliographical note

Keywords

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