Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst

Bo Liang Zhao; Da Ming Du

doi:10.1016/j.tetasy.2014.01.005

Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst

Bo Liang Zhao, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

27 Citations (Scopus)

Abstract

The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary.

Original language	English
Pages (from-to)	310-317
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	25
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2014.01.005
Publication status	Published - 28 Feb 2014

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abstract = "The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88\% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary.",

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AU - Zhao, Bo Liang

AU - Du, Da Ming

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N2 - The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary.

AB - The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with α,β-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary.

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DO - 10.1016/j.tetasy.2014.01.005

M3 - Article

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VL - 25

SP - 310

EP - 317

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst

Abstract

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