Squaramide-tertiary amine catalyzed asymmetric cascade sulfa-Michael/ Michael addition via dynamic kinetic resolution: Access to highly functionalized chromans with three contiguous stereocenters

Wen Yang; Yi Yang; Da Ming Du

doi:10.1021/ol400025a

Squaramide-tertiary amine catalyzed asymmetric cascade sulfa-Michael/ Michael addition via dynamic kinetic resolution: Access to highly functionalized chromans with three contiguous stereocenters

Wen Yang, Yi Yang, 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

92 Citations (Scopus)

Abstract

An efficient asymmetric cascade sulfa-Michael/Michael addition reaction catalyzed by a chiral bifunctional squaramide-tertiary amine catalyst has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chromans with three contiguous stereocenters, including one quaternary center. In addition, a novel cascade sulfa Michael/retro-sulfa- Michael/sulfa-Michael/Michael reaction process, involving dynamic kinetic resolution, is described.

Original language	English
Pages (from-to)	1190-1193
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	6
DOIs	https://doi.org/10.1021/ol400025a
Publication status	Published - 15 Mar 2013

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abstract = "An efficient asymmetric cascade sulfa-Michael/Michael addition reaction catalyzed by a chiral bifunctional squaramide-tertiary amine catalyst has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chromans with three contiguous stereocenters, including one quaternary center. In addition, a novel cascade sulfa Michael/retro-sulfa- Michael/sulfa-Michael/Michael reaction process, involving dynamic kinetic resolution, is described.",

author = "Wen Yang and Yi Yang and Du, {Da Ming}",

year = "2013",

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doi = "10.1021/ol400025a",

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journal = "Organic Letters",

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T1 - Squaramide-tertiary amine catalyzed asymmetric cascade sulfa-Michael/ Michael addition via dynamic kinetic resolution

T2 - Access to highly functionalized chromans with three contiguous stereocenters

AU - Yang, Wen

AU - Yang, Yi

AU - Du, Da Ming

PY - 2013/3/15

Y1 - 2013/3/15

N2 - An efficient asymmetric cascade sulfa-Michael/Michael addition reaction catalyzed by a chiral bifunctional squaramide-tertiary amine catalyst has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chromans with three contiguous stereocenters, including one quaternary center. In addition, a novel cascade sulfa Michael/retro-sulfa- Michael/sulfa-Michael/Michael reaction process, involving dynamic kinetic resolution, is described.

AB - An efficient asymmetric cascade sulfa-Michael/Michael addition reaction catalyzed by a chiral bifunctional squaramide-tertiary amine catalyst has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chromans with three contiguous stereocenters, including one quaternary center. In addition, a novel cascade sulfa Michael/retro-sulfa- Michael/sulfa-Michael/Michael reaction process, involving dynamic kinetic resolution, is described.

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U2 - 10.1021/ol400025a

DO - 10.1021/ol400025a

M3 - Article

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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Squaramide-tertiary amine catalyzed asymmetric cascade sulfa-Michael/ Michael addition via dynamic kinetic resolution: Access to highly functionalized chromans with three contiguous stereocenters

Abstract

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