Enantioselective Thiolysis and Aminolysis of Cyclic Anhydrides Using a Chiral Diamine-Derived Thiourea Catalyst

Jae Ho Shim, Sung Joo Park, Byung Kook Ahn, Ji Yeon Lee, Hyeon Soo Kim, Deok Chan Ha

Research output: Contribution to journalArticlepeer-review

Abstract

Catalytic desymmetrization of cyclic anhydrides has been widely investigated in the field of organocatalysis. Using this approach, many stereocenters can be established in a single, symmetry-breaking transformation. Herein, a thiourea organocatalyst was prepared in a single step from a chiral diamine, (R,R)-1,2-diphenylethylenediamine, and used for the desymmetrization of various cyclic anhydrides through double hydrogen-bonding activation. The asymmetric ring-opening reaction of the cyclic anhydride proceeded via the enantioselective addition reaction catalyzed by diamine thiourea. Thiolysis afforded the desired products in the yields of 86–98% and enantioselectivities of 60–94%, while aminolysis afforded the yields of 90–94% and enantioselectivities of 90–95%.

Original languageEnglish
Pages (from-to)34501-34511
Number of pages11
JournalACS Omega
Volume6
Issue number50
DOIs
Publication statusPublished - 2021 Dec 21

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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