Squaramide-catalyzed diastereo- and enantioselective Michael addition of 3-substituted oxindoles to nitroalkenes

Wen Yang; Jingsi Wang; Da Ming Du

doi:10.1016/j.tetasy.2012.06.018

Squaramide-catalyzed diastereo- and enantioselective Michael addition of 3-substituted oxindoles to nitroalkenes

Wen Yang, Jingsi Wang, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

27 Citations (Scopus)

Abstract

An efficient diastereo- and enantioselective Michael addition of 3-substituted oxindoles onto nitroalkenes catalyzed by a bifunctional chiral squaramide catalyst has been developed. This organocatalytic reaction with 2 mol % of catalyst proceeded smoothly to afford 3,3-disubstituted oxindoles in high yields with good diastereoselectivities and enantioselectivities (up to 98:2 dr, 88% ee).

Original language	English
Pages (from-to)	972-980
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	23
Issue number	13
DOIs	https://doi.org/10.1016/j.tetasy.2012.06.018
Publication status	Published - 15 Jul 2012

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10.1016/j.tetasy.2012.06.018

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title = "Squaramide-catalyzed diastereo- and enantioselective Michael addition of 3-substituted oxindoles to nitroalkenes",

abstract = "An efficient diastereo- and enantioselective Michael addition of 3-substituted oxindoles onto nitroalkenes catalyzed by a bifunctional chiral squaramide catalyst has been developed. This organocatalytic reaction with 2 mol % of catalyst proceeded smoothly to afford 3,3-disubstituted oxindoles in high yields with good diastereoselectivities and enantioselectivities (up to 98:2 dr, 88% ee).",

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AU - Yang, Wen

AU - Wang, Jingsi

AU - Du, Da Ming

PY - 2012/7/15

Y1 - 2012/7/15

N2 - An efficient diastereo- and enantioselective Michael addition of 3-substituted oxindoles onto nitroalkenes catalyzed by a bifunctional chiral squaramide catalyst has been developed. This organocatalytic reaction with 2 mol % of catalyst proceeded smoothly to afford 3,3-disubstituted oxindoles in high yields with good diastereoselectivities and enantioselectivities (up to 98:2 dr, 88% ee).

AB - An efficient diastereo- and enantioselective Michael addition of 3-substituted oxindoles onto nitroalkenes catalyzed by a bifunctional chiral squaramide catalyst has been developed. This organocatalytic reaction with 2 mol % of catalyst proceeded smoothly to afford 3,3-disubstituted oxindoles in high yields with good diastereoselectivities and enantioselectivities (up to 98:2 dr, 88% ee).

UR - http://www.scopus.com/inward/record.url?scp=84864672258&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2012.06.018

DO - 10.1016/j.tetasy.2012.06.018

M3 - Article

AN - SCOPUS:84864672258

SN - 0957-4166

VL - 23

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EP - 980

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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ER -

Squaramide-catalyzed diastereo- and enantioselective Michael addition of 3-substituted oxindoles to nitroalkenes

Abstract

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