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

Authors
Shim, Jae HoPark, Sung JooAhn, Byung KookLee, Ji YeonKim, Hyeon SooHa, Deok-Chan
Issue Date
21-12월-2021
Publisher
AMER CHEMICAL SOC
Citation
ACS OMEGA, v.6, no.50, pp.34501 - 34511
Indexed
SCIE
SCOPUS
Journal Title
ACS OMEGA
Volume
6
Number
50
Start Page
34501
End Page
34511
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/137622
DOI
10.1021/acsomega.1c04741
ISSN
2470-1343
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%.
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