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

Bar-Ilan University

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.

Funding

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.

Funders	Funder number
Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University
Israel Science Foundation

Keywords

Asymmetric induction
Butenolides
Cyclopentenecarboxylates
Lithium ion chelation
Michael reactions

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10.1016/s0040-4039(00)00867-4

Cite this

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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.",

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

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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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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

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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

Funding

Keywords

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