Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

Miao Ding; Feng Zhou; Yun Lin Liu; Cui Hong Wang; Xiao Li Zhao; Jian Zhou

doi:10.1039/c1sc00390a

Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

Miao Ding
, Feng Zhou
, Yun Lin Liu
, Cui Hong Wang
, Xiao Li Zhao
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

180 Scopus citations

Abstract

A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21:1 diastereoselectivity and up to 99% enantioselectivity.

Original language	English
Pages (from-to)	2035-2039
Number of pages	5
Journal	Chemical Science
Volume	2
Issue number	10
DOIs	https://doi.org/10.1039/c1sc00390a
State	Published - Oct 2011

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title = "Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins",

abstract = "A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21:1 diastereoselectivity and up to 99\% enantioselectivity.",

author = "Miao Ding and Feng Zhou and Liu, \{Yun Lin\} and Wang, \{Cui Hong\} and Zhao, \{Xiao Li\} and Jian Zhou",

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pages = "2035--2039",

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AU - Ding, Miao

AU - Zhou, Feng

AU - Liu, Yun Lin

AU - Wang, Cui Hong

AU - Zhao, Xiao Li

AU - Zhou, Jian

PY - 2011/10

Y1 - 2011/10

N2 - A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21:1 diastereoselectivity and up to 99% enantioselectivity.

AB - A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21:1 diastereoselectivity and up to 99% enantioselectivity.

UR - https://www.scopus.com/pages/publications/80054103574

U2 - 10.1039/c1sc00390a

DO - 10.1039/c1sc00390a

M3 - 文章

AN - SCOPUS:80054103574

SN - 2041-6520

VL - 2

SP - 2035

EP - 2039

JO - Chemical Science

JF - Chemical Science

IS - 10

ER -

Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

Abstract

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