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Title: Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles
Authors: Liu, Changyi
Wu, Shuquan
Xu, Jun
Chen, Lingzhu
Zheng, Pengcheng
Chi, Robin Yonggui
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2019
Source: Liu, C., Wu, S., Xu, J., Chen, L., Zheng, P., & Chi, R. Y. (2019). Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles. Organic Letters, 21(23), 9493-9496. doi:10.1021/acs.orglett.9b03685
Journal: Organic Letters
Abstract: A carbene-catalyzed reaction between α-bromoenals and thioamides was developed. Key steps include enantioselective 1,4-addition of thioamide sulfur atoms to α,β-unsaturated acyl azolium intermediate. Subsequent intramolecular annulation eventually affords thiazinone heterocycles with high optical purities. The introduction of Lewis acid additives such as Cu(OTf)2 to this NHC catalytic reaction could provide small but consistent improvements to reaction enantioselectivities.
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.9b03685
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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