Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 19, Pages 10971-10976Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202101569
Keywords
chiral primary amines; disulfuration; enamines; frustrated Lewis pairs; organocatalysis
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Funding
- Natural Science Foundation of China [21672217, 21861132003, 22031006]
- Tsinghua University Initiative Scientific Research Program
- National Program of Topnotch Young Professionals
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A novel three-component Lewis acid-base catalyst has been developed, utilizing a bulky tertiary amine to activate a Lewis pair for enamine catalysis, allowing for asymmetric control of disulfuration reactions.
A three-component Lewis acid-base (Lewis trio) involving a bulky chiral primary amine, B(C6F5)(3) and a bulky tertiary amine has been developed as an effective enamine catalyst for enantioselective disulfuration reactions. The bulky tertiary amine was found to activate a bulky primary-tertiary diamine-borane Lewis pair for enamine catalysis via frustrated interaction. The resulted chiral bulky Lewis trio (BLT) allows for the construction of chiral disulfides via direct disulfuration with beta-ketocarbonyls or alpha-branched aldehydes in a practical and highly stereocontrolled manner.
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