Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles

Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles

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 pu...

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Bibliographic Details
Main Authors: Liu, Changyi, Wu, Shuquan, Xu, Jun, Chen, Lingzhu, Zheng, Pengcheng, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Enantioselective Addition
Carbene-catalyzed
Online Access:https://hdl.handle.net/10356/137760
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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