期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 15, 页码 4522-4526出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409894
关键词
asymmetric catalysis; organocatalysis; ortho-quinone methides; thiol addition
资金
- Natural Science Foundation of China [21322202, 21472187]
- National Basic Research Program of China [2010CB833300]
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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