Catalytic asymmetric direct vinylogous michael addition of deconjugated butenolides to maleimides for the construction of quaternary stereogenic centers

Madhu Sudan Manna; Santanu Mukherjee

doi:10.1002/chem.201203180

Catalytic asymmetric direct vinylogous michael addition of deconjugated butenolides to maleimides for the construction of quaternary stereogenic centers

Madhu Sudan Manna, Santanu Mukherjee

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

71 Scopus citations

Abstract

Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).

Original language	English (US)
Pages (from-to)	15277-15282
Number of pages	6
Journal	Chemistry - A European Journal
Volume	18
Issue number	48
DOIs	https://doi.org/10.1002/chem.201203180
State	Published - Nov 26 2012
Externally published	Yes

Keywords

asymmetric catalysis
butyrolactone
maleimide
Michael addition
thiourea

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201203180

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abstract = "Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).",

keywords = "asymmetric catalysis, butyrolactone, maleimide, Michael addition, thiourea",

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doi = "10.1002/chem.201203180",

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AU - Mukherjee, Santanu

PY - 2012/11/26

Y1 - 2012/11/26

N2 - Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).

AB - Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).

KW - asymmetric catalysis

KW - butyrolactone

KW - maleimide

KW - Michael addition

KW - thiourea

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Catalytic asymmetric direct vinylogous michael addition of deconjugated butenolides to maleimides for the construction of quaternary stereogenic centers

Abstract

Keywords

ASJC Scopus subject areas

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