Remarkable influence of secondary catalyst site on enantioselective desymmetrization of cyclopentenedione

An efficient, robust and highly enantioselective catalytic desymmetrization of 2,2-disubstituted cyclopentene-1,3-diones is developed viadirect vinylogous nucleophilic addition of deconjugated butenolides. A remarkable influence of the secondary catalyst site on the enantioselectivity points towards...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2014-01, Vol.5 (4), p.1627-1633
Main Authors: Manna, Madhu Sudan, Mukherjee, Santanu
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
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Summary:An efficient, robust and highly enantioselective catalytic desymmetrization of 2,2-disubstituted cyclopentene-1,3-diones is developed viadirect vinylogous nucleophilic addition of deconjugated butenolides. A remarkable influence of the secondary catalyst site on the enantioselectivity points towards an intriguing mechanistic scenario, possibly by triggering a change in catalyst conformation.
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc53102c