Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 63, Pages 16747-16752Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803703
Keywords
asymmetric synthesis; lactonizations; organocatalysis; sulfides; transition states
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Funding
- JSPS KAKENHI [JP16K05780, JP17KT0011, JP18H04660]
- Cooperative Research Program of Network Joint Research Center for Materials and Devices [20181268]
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Although a wide variety of chiral organocatalysts have been developed for asymmetric transformations, effective chiral dialkyl sulfide organocatalysts remain relatively rare and under-developed, despite the potential utility of dialkyl sulfide catalysts. Herein, we report the development of chiral bifunctional dialkyl sulfide catalysts possessing a urea moiety for regio-, diastereo-, and enantioselective bromolactonization. The importance of the bifunctional design of chiral sulfide catalysts was clearly demonstrated in the present work. The roles of both the sulfide and urea moieties of the catalyst were clarified based on the results of experimental and theoretical investigation.
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