Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes

Utpal Das; Yi Ru Chen; Yi Ling Tsai; Wen-Wei Lin

doi:10.1002/chem.201301332

Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes

Utpal Das, Yi Ru Chen, Yi Ling Tsai, Wen-Wei Lin

Department of Chemistry

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

47 Citations (Scopus)

Abstract

Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).

Original language	English
Pages (from-to)	7713-7717
Number of pages	5
Journal	Chemistry - A European Journal
Volume	19
Issue number	24
DOIs	https://doi.org/10.1002/chem.201301332
Publication status	Published - 2013 Jun 10

Keywords

Michael addition
cinchona alkaloids
organocatalysis
quaternary stereogenic center
γ-butenolides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201301332

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abstract = "Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).",

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AU - Tsai, Yi Ling

AU - Lin, Wen-Wei

PY - 2013/6/10

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AB - Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).

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KW - cinchona alkaloids

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