An organocatalytic asymmetric tandem reaction for the construction of bicyclic skeletons

Chun Li Cao; You Yun Zhou; Jian Zhou; Xiu Li Sun; Yong Tang; Yu Xue Li; Guang Yu Li; Jie Sun

doi:10.1002/chem.200900696

An organocatalytic asymmetric tandem reaction for the construction of bicyclic skeletons

Chun Li Cao, You Yun Zhou, Jian Zhou, Xiu Li Sun, Yong Tang, Yu Xue Li, Guang Yu Li, Jie Sun

CAS - Shanghai Institute of Organic Chemistry

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

104 Scopus citations

Abstract

Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98% ee in moderate to high yields. The cooperative effects of both enamine and the Brønsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.

Original language	English
Pages (from-to)	11384-11389
Number of pages	6
Journal	Chemistry - A European Journal
Volume	15
Issue number	42
DOIs	https://doi.org/10.1002/chem.200900696
State	Published - 26 Oct 2009
Externally published	Yes

Keywords

Bifunctional catalysts
Density functional calculations
Ketones
Organocatalysis
Tandem reactions

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10.1002/chem.200900696

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title = "An organocatalytic asymmetric tandem reaction for the construction of bicyclic skeletons",

abstract = "Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98\% ee in moderate to high yields. The cooperative effects of both enamine and the Br{\o}nsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.",

keywords = "Bifunctional catalysts, Density functional calculations, Ketones, Organocatalysis, Tandem reactions",

author = "Cao, \{Chun Li\} and Zhou, \{You Yun\} and Jian Zhou and Sun, \{Xiu Li\} and Yong Tang and Li, \{Yu Xue\} and Li, \{Guang Yu\} and Jie Sun",

year = "2009",

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T1 - An organocatalytic asymmetric tandem reaction for the construction of bicyclic skeletons

AU - Cao, Chun Li

AU - Zhou, You Yun

AU - Zhou, Jian

AU - Sun, Xiu Li

AU - Tang, Yong

AU - Li, Yu Xue

AU - Li, Guang Yu

AU - Sun, Jie

PY - 2009/10/26

Y1 - 2009/10/26

N2 - Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98% ee in moderate to high yields. The cooperative effects of both enamine and the Brønsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.

AB - Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98% ee in moderate to high yields. The cooperative effects of both enamine and the Brønsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.

KW - Bifunctional catalysts

KW - Density functional calculations

KW - Ketones

KW - Organocatalysis

KW - Tandem reactions

UR - https://www.scopus.com/pages/publications/70350509611

U2 - 10.1002/chem.200900696

DO - 10.1002/chem.200900696

M3 - 文章

AN - SCOPUS:70350509611

SN - 0947-6539

VL - 15

SP - 11384

EP - 11389

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 42

ER -

An organocatalytic asymmetric tandem reaction for the construction of bicyclic skeletons

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Keywords

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