Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via morita-baylis-hillman reaction

Yun Lin Liu; Bo Lun Wang; Jun Jie Cao; Long Chen; Yong Xue Zhang; Chao Wang; Jian Zhou

doi:10.1021/ja107858z

Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via morita-baylis-hillman reaction

Yun Lin Liu
, Bo Lun Wang
, Jun Jie Cao
, Long Chen
, Yong Xue Zhang
, Chao Wang
, Jian Zhou^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

245 引用（Scopus）

摘要

We report a highly enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins and acrolein to provide enantiomerically enriched 3-substituted 3-hydroxyoxindoles, which could serve as valuable synthetic building blocks. This is also the first time that a ketone has been used as the electrophile and acrolein as the nucleophile in a highly enantioselective catalytic asymmetric MBH reaction. Hatakeyama's catalyst, β-isocupreidine (1), turned out to be a powerful catalyst for this transformation.

源语言	英语
页（从-至）	15176-15178
页数	3
期刊	Journal of the American Chemical Society
卷	132
期	43
DOI	https://doi.org/10.1021/ja107858z
出版状态	已出版 - 3 11月 2010

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abstract = "We report a highly enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins and acrolein to provide enantiomerically enriched 3-substituted 3-hydroxyoxindoles, which could serve as valuable synthetic building blocks. This is also the first time that a ketone has been used as the electrophile and acrolein as the nucleophile in a highly enantioselective catalytic asymmetric MBH reaction. Hatakeyama's catalyst, β-isocupreidine (1), turned out to be a powerful catalyst for this transformation.",

author = "Liu, \{Yun Lin\} and Wang, \{Bo Lun\} and Cao, \{Jun Jie\} and Long Chen and Zhang, \{Yong Xue\} and Chao Wang and Jian Zhou",

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T1 - Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via morita-baylis-hillman reaction

AU - Liu, Yun Lin

AU - Wang, Bo Lun

AU - Cao, Jun Jie

AU - Chen, Long

AU - Zhang, Yong Xue

AU - Wang, Chao

AU - Zhou, Jian

PY - 2010/11/3

Y1 - 2010/11/3

N2 - We report a highly enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins and acrolein to provide enantiomerically enriched 3-substituted 3-hydroxyoxindoles, which could serve as valuable synthetic building blocks. This is also the first time that a ketone has been used as the electrophile and acrolein as the nucleophile in a highly enantioselective catalytic asymmetric MBH reaction. Hatakeyama's catalyst, β-isocupreidine (1), turned out to be a powerful catalyst for this transformation.

AB - We report a highly enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins and acrolein to provide enantiomerically enriched 3-substituted 3-hydroxyoxindoles, which could serve as valuable synthetic building blocks. This is also the first time that a ketone has been used as the electrophile and acrolein as the nucleophile in a highly enantioselective catalytic asymmetric MBH reaction. Hatakeyama's catalyst, β-isocupreidine (1), turned out to be a powerful catalyst for this transformation.

UR - https://www.scopus.com/pages/publications/78049397718

U2 - 10.1021/ja107858z

DO - 10.1021/ja107858z

M3 - 文章

AN - SCOPUS:78049397718

SN - 0002-7863

VL - 132

SP - 15176

EP - 15178

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 43

ER -

Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via morita-baylis-hillman reaction

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