Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 42, Pages 11384-11389Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900696
Keywords
bifunctional catalysts; density functional calculations; ketones; organocatalysis; tandem reactions
Categories
Funding
- Natural Sciences Foundation of China [20821002, 20672131]
- Major State Basic Research Development Program [2009CB825300]
- Chinese Academy of Sciences
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Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98% ee in moderate to high yields. The cooperative effects of both enamine and the Bronsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.
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