Catalytic Asymmetric Direct Vinylogous Michael Addition of Deconjugated Butenolides to Maleimides for the Construction of Quaternary Stereogenic Centers

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-11, Vol.18 (48), p.15277-15282
Main Authors: Manna, Madhu Sudan, Mukherjee, Santanu
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
asymmetric catalysis
butyrolactone
Catalysis
Chemistry
maleimide
Maleimides - chemistry
Michael addition
Molecular Structure
Stereoisomerism
Succinimides - chemical synthesis
Succinimides - chemistry
thiourea
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Summary: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).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201203180