A Convenient One-Pot Synthesis of Both Enantiomers of 1,3,5-Trisubstituted Hydantoins

Abstract A novel one-pot asymmetric synthetic method for the direct conversion of bromoacetates into highly substituted hydantoins has been developed. Both enantiomers of 1,3,5-trisubstituted hydantoins were conveniently synthesized through a dynamic kinetic resolution of bromoacetates derived from...

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Bibliographic Details
Published in:Synlett 2020, Vol.31 (2), p.171-174
Main Authors: Han, Gun Hee, Kim, Seo Yun, Lee, Ha Rim, Lee, Ji Su, Park, Yong Sun
Format: Article
Language:English
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Summary:Abstract A novel one-pot asymmetric synthetic method for the direct conversion of bromoacetates into highly substituted hydantoins has been developed. Both enantiomers of 1,3,5-trisubstituted hydantoins were conveniently synthesized through a dynamic kinetic resolution of bromoacetates derived from either ethyl l -lactate or diacetone- d -glucose. The sequential three-component reaction permitted the preparation of ( R )- or ( S )-1,3,5-trisubstituted hydantoins in yields of 77–51% with enantiomeric ratios of up to 95:5.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0039-1691406