Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins

A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocente...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2012-01, Vol.48 (42), p.5193-5195
Main Authors: Manna, Madhu Sudan, Kumar, Vikas, Mukherjee, Santanu
Format: Article
Language:English
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Summary:A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20:1 dr) and high enantioselectivity (up to 99:1 er).
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc31700a