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 language | English |
|---|---|
| Pages (from-to) | 34501-34511 |
| Number of pages | 11 |
| Journal | ACS Omega |
| Volume | 6 |
| Issue number | 50 |
| DOIs | |
| Publication status | Published - 2021 Dec 21 |
Bibliographical note
Funding Information:This study was supported by the National Research Foundation (NRF) and funded by the Korean government (MSIT) (2021R1A6A3A01087948). This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) and funded by the Korean government (MSIT) (2021M3A9G1097744). Also, this study was supported by a Korea University grant. We are grateful for the financial support provided by Dr. K. H. Kim.
Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society
ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)