4.8 Article

Remarkable influence of secondary catalyst site on enantioselective desymmetrization of cyclopentenedione

Journal

CHEMICAL SCIENCE
Volume 5, Issue 4, Pages 1627-1633

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc53102c

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Funding

  1. Department of Science and Technology (DST), New Delhi [SR/FT/CS-90/2010]
  2. Council of Scientific and Industrial Research (CSIR), New Delhi [01 (2505)/11/EMR-II]
  3. CSIR

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An efficient, robust and highly enantioselective catalytic desymmetrization of 2,2-disubstituted cyclopentene-1,3-diones is developed via direct 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.

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