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

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%.

SUBMITTER: Shim JH

PROVIDER: S-EPMC8697410 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Shim Jae Ho JH Park Sung Joo SJ Ahn Byung Kook BK Lee Ji Yeon JY Kim Hyeon Soo HS Ha Deok-Chan DC

ACS omega 20211124 50

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 t ...[more]

PMID: 34963935

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