A highly stereoselective hydrogen-bond-mediated Michael-Michael cascade process through dynamic kinetic resolution

Jian Wang; Hexin Xie; Hao Li; Liansuo Zu; Wei Wang

doi:10.1002/anie.200800381

A highly stereoselective hydrogen-bond-mediated Michael-Michael cascade process through dynamic kinetic resolution

Jian Wang, Hexin Xie, Hao Li, Liansuo Zu, Wei Wang

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

175 Scopus citations

Abstract

(Chemical Equation Presented) Oh Mickey, you're so fine: The title reaction, which is efficiently catalyzed by a cinchona alkaloid thioure affords direct access to thiochromanes in high efficiency. The reaction features a new activation mode of organocatalytic dynamic kinetic resolution involving a Michael-retro-Michael-Michael-Michael cascade.

Original language	English (US)
Pages (from-to)	4177-4179
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	22
DOIs	https://doi.org/10.1002/anie.200800381
State	Published - May 19 2008
Externally published	Yes

Keywords

Cascade reactions
Kinetic dynamic resolution
Michael addition
Organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200800381

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title = "A highly stereoselective hydrogen-bond-mediated Michael-Michael cascade process through dynamic kinetic resolution",

abstract = "(Chemical Equation Presented) Oh Mickey, you're so fine: The title reaction, which is efficiently catalyzed by a cinchona alkaloid thioure affords direct access to thiochromanes in high efficiency. The reaction features a new activation mode of organocatalytic dynamic kinetic resolution involving a Michael-retro-Michael-Michael-Michael cascade.",

keywords = "Cascade reactions, Kinetic dynamic resolution, Michael addition, Organocatalysis",

author = "Jian Wang and Hexin Xie and Hao Li and Liansuo Zu and Wei Wang",

year = "2008",

month = may,

day = "19",

doi = "10.1002/anie.200800381",

language = "English (US)",

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pages = "4177--4179",

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T1 - A highly stereoselective hydrogen-bond-mediated Michael-Michael cascade process through dynamic kinetic resolution

AU - Wang, Jian

AU - Xie, Hexin

AU - Li, Hao

AU - Zu, Liansuo

AU - Wang, Wei

PY - 2008/5/19

Y1 - 2008/5/19

N2 - (Chemical Equation Presented) Oh Mickey, you're so fine: The title reaction, which is efficiently catalyzed by a cinchona alkaloid thioure affords direct access to thiochromanes in high efficiency. The reaction features a new activation mode of organocatalytic dynamic kinetic resolution involving a Michael-retro-Michael-Michael-Michael cascade.

AB - (Chemical Equation Presented) Oh Mickey, you're so fine: The title reaction, which is efficiently catalyzed by a cinchona alkaloid thioure affords direct access to thiochromanes in high efficiency. The reaction features a new activation mode of organocatalytic dynamic kinetic resolution involving a Michael-retro-Michael-Michael-Michael cascade.

KW - Cascade reactions

KW - Kinetic dynamic resolution

KW - Michael addition

KW - Organocatalysis

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U2 - 10.1002/anie.200800381

DO - 10.1002/anie.200800381

M3 - Article

AN - SCOPUS:53549133989

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EP - 4179

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 22

ER -

A highly stereoselective hydrogen-bond-mediated Michael-Michael cascade process through dynamic kinetic resolution

Abstract

Keywords

ASJC Scopus subject areas

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