Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 15, Pages 4522-4526Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409894
Keywords
asymmetric catalysis; organocatalysis; ortho-quinone methides; thiol addition
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Funding
- Natural Science Foundation of China [21322202, 21472187]
- National Basic Research Program of China [2010CB833300]
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The enantioselective conjugated addition of tritylthiol to insitu generated ortho-quinone methides (o-QMs) is catalyzed by an acid-base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99%) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a new strategy for the synthesis of optically active benzyl mercaptans. Control experiments suggested that o-QMs are generated by the tertiary amine moiety of the squaramide organocatalyst and that the water-oil biphase is crucial for achieving high reactivity and stereoselectivity.
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