Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

Jin Sheng Yu; Feng Zhou; Yun Lin Liu; Jian Zhou

doi:10.3762/bjoc.8.157

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

Jin Sheng Yu, Feng Zhou, Yun Lin Liu, Jian Zhou

School of Chemistry and Molecular Engineering

East China Normal University

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

34 Scopus citations

Abstract

We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD) ₂PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented.

Original language	English
Pages (from-to)	1360-1365
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	8
DOIs	https://doi.org/10.3762/bjoc.8.157
State	Published - 23 Aug 2012

Keywords

3,3-disubstituted oxindoles
Michael addition
Organocatalysis
Quaternary stereogenic center
Unprotected 3-substituted oxindoles

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title = "Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone",

abstract = "We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD) 2PYR was found to be able to catalyze this reaction in up to 83\% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented.",

keywords = "3,3-disubstituted oxindoles, Michael addition, Organocatalysis, Quaternary stereogenic center, Unprotected 3-substituted oxindoles",

author = "Yu, \{Jin Sheng\} and Feng Zhou and Liu, \{Yun Lin\} and Jian Zhou",

year = "2012",

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T1 - Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

AU - Yu, Jin Sheng

AU - Zhou, Feng

AU - Liu, Yun Lin

AU - Zhou, Jian

PY - 2012/8/23

Y1 - 2012/8/23

N2 - We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD) 2PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented.

AB - We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD) 2PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented.

KW - 3,3-disubstituted oxindoles

KW - Michael addition

KW - Organocatalysis

KW - Quaternary stereogenic center

KW - Unprotected 3-substituted oxindoles

UR - https://www.scopus.com/pages/publications/84865589997

U2 - 10.3762/bjoc.8.157

DO - 10.3762/bjoc.8.157

M3 - 文章

AN - SCOPUS:84865589997

SN - 2195-951X

VL - 8

SP - 1360

EP - 1365

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

Abstract

Keywords

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