Synthesis of highly functionalized chiral 3,3′-disubstituted oxindoles via an organocatalytic enantioselective Michael addition of nitroalkanes to indolylidenecyanoacetates

Lu Liu; Deyan Wu; Shu Zheng; Tengfei Li; Xiangmin Li; Sinan Wang; Jian Li; Hao Li; Wei Wang

doi:10.1021/ol202931e

Synthesis of highly functionalized chiral 3,3′-disubstituted oxindoles via an organocatalytic enantioselective Michael addition of nitroalkanes to indolylidenecyanoacetates

Lu Liu
, Deyan Wu
, Shu Zheng
, Tengfei Li
, Xiangmin Li
, Sinan Wang
, Jian Li
, Hao Li
, Wei Wang

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

32 Scopus citations

Abstract

An efficient bifunctional cinchona alkaloid derived thiourea-promoted enantioselective conjugate addition of nitroalkanes to indolylidenecyanoacetates has been developed under neat conditions. The process leads to synthetically interesting densely functionalized 3,3′-disubstituted oxindoles with creation of up to three stereogenic centers.

Original language	English (US)
Pages (from-to)	134-137
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	1
DOIs	https://doi.org/10.1021/ol202931e
State	Published - Jan 6 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An efficient bifunctional cinchona alkaloid derived thiourea-promoted enantioselective conjugate addition of nitroalkanes to indolylidenecyanoacetates has been developed under neat conditions. The process leads to synthetically interesting densely functionalized 3,3′-disubstituted oxindoles with creation of up to three stereogenic centers.",

author = "Lu Liu and Deyan Wu and Shu Zheng and Tengfei Li and Xiangmin Li and Sinan Wang and Jian Li and Hao Li and Wei Wang",

year = "2012",

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AU - Liu, Lu

AU - Wu, Deyan

AU - Zheng, Shu

AU - Li, Tengfei

AU - Li, Xiangmin

AU - Wang, Sinan

AU - Li, Jian

AU - Li, Hao

AU - Wang, Wei

PY - 2012/1/6

Y1 - 2012/1/6

N2 - An efficient bifunctional cinchona alkaloid derived thiourea-promoted enantioselective conjugate addition of nitroalkanes to indolylidenecyanoacetates has been developed under neat conditions. The process leads to synthetically interesting densely functionalized 3,3′-disubstituted oxindoles with creation of up to three stereogenic centers.

AB - An efficient bifunctional cinchona alkaloid derived thiourea-promoted enantioselective conjugate addition of nitroalkanes to indolylidenecyanoacetates has been developed under neat conditions. The process leads to synthetically interesting densely functionalized 3,3′-disubstituted oxindoles with creation of up to three stereogenic centers.

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U2 - 10.1021/ol202931e

DO - 10.1021/ol202931e

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Synthesis of highly functionalized chiral 3,3′-disubstituted oxindoles via an organocatalytic enantioselective Michael addition of nitroalkanes to indolylidenecyanoacetates

Abstract

ASJC Scopus subject areas

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