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- Title
Biocatalytic Thionation of Epoxides for Enantioselective Synthesis of Thiiranes.
- Authors
Ma, Ran; Hua, Xia; He, Cheng‐Li; Wang, Hui‐Hui; Wang, Zhu‐Xiang; Cui, Bao‐Dong; Han, Wen‐Yong; Chen, Yong‐Zheng; Wan, Nan‐Wei
- Abstract
Expanding the enzymatic toolbox for the green synthesis of valuable molecules is still of high interest in synthetic chemistry and the pharmaceutical industry. Chiral thiiranes are valuable sulfur‐containing heterocyclic compounds, but relevant methods for their enantioselective synthesis are limited. Herein, we report a biocatalytic thionation strategy for the enantioselective synthesis of thiiranes, which was developed based on the halohydrin dehalogenase (HHDH)‐catalyzed enantioselective ring‐opening reaction of epoxides with thiocyanate and a subsequent nonenzymatic rearrangement process. A novel HHDH was identified and engineered for enantioselective biocatalytic thionation of various aryl‐ and alkyl‐substituted epoxides on a preparative scale, affording the corresponding thiiranes in up to 43 % isolated yield and 98 % ee. Large‐scale synthesis and useful transformations of chiral thiiranes were also performed to demonstrate the utility and scalability of the biocatalytic thionation strategy.
- Subjects
SULFURATION; EPOXY compounds; RING-opening reactions; PHARMACEUTICAL chemistry; HETEROCYCLIC compounds
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 52, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202212589