Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 5, Pages 1777-1781Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510457
Keywords
annulations; enantioselectivity; heterocycles; organocatalysis; synthetic methods
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Funding
- DST, Government of India [SR/FT/CS-156/2011]
- IISER Mohali
- UGC, New Delhi
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The first enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (MBH) reaction of sterically highly demanding beta,beta-disubstituted enones is presented. The MBH reaction of beta,beta-disubstituted-alpha,beta-unsaturated electron-withdrawing systems was previously considered to be unfeasible. Towards this end, designer substrates, which under simple and practical reaction conditions generate a variety of cyclopenta[b]annulated arenes and heteroarenes in excellent enantiopurities and near-quantitative yields in remarkably short reaction times, are described. The reason for the unusually facile nature of this reaction is attributed to the synergy guided and entropically favored intramolecular reaction. Further, this strategy provides easy access to a substantial number of bioactive natural products and pharmaceutically significant compounds.
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