Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas

Jae Ho Shim, Min Ji Lee, Min Ho Lee, Byeong Seon Kim, Deok Chan Ha

Research output: Contribution to journalArticle

Abstract

Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, (R)-Phenibut.

Original languageEnglish
Pages (from-to)31808-31814
Number of pages7
JournalRSC Advances
Volume10
Issue number53
DOIs
Publication statusPublished - 2020 Aug 27

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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