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

29 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

Access to Document

10.1021/ol202931e

Cite this

@article{94109d9b068345fb85bbf2220908a7ee,

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

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",

month = jan,

day = "6",

doi = "10.1021/ol202931e",

language = "English (US)",

volume = "14",

pages = "134--137",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Synthesis of highly functionalized chiral 3,3′-disubstituted oxindoles via an organocatalytic enantioselective Michael addition of nitroalkanes to indolylidenecyanoacetates

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.

UR - http://www.scopus.com/inward/record.url?scp=84862909339&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862909339&partnerID=8YFLogxK

U2 - 10.1021/ol202931e

DO - 10.1021/ol202931e

M3 - Article

C2 - 22149210

AN - SCOPUS:84862909339

SN - 1523-7060

VL - 14

SP - 134

EP - 137

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this