Carbene-Catalyzed Enantioselective Addition of Thioamides to Bromoenals for Access to Thiazinone Heterocycles

Changyi Liu; Shuquan Wu; Jun Xu; Lingzhu Chen; Pengcheng Zheng; Yonggui Robin Chi

doi:10.1021/acs.orglett.9b03685

Carbene-Catalyzed Enantioselective Addition of Thioamides to Bromoenals for Access to Thiazinone Heterocycles

Changyi Liu, Shuquan Wu, Jun Xu, Lingzhu Chen, Pengcheng Zheng^*, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

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.

Original language	English
Pages (from-to)	9493-9496
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.9b03685
Publication status	Published - Dec 6 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b03685

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title = "Carbene-Catalyzed Enantioselective Addition of Thioamides to Bromoenals for Access to Thiazinone Heterocycles",

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.",

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AU - Liu, Changyi

AU - Wu, Shuquan

AU - Xu, Jun

AU - Chen, Lingzhu

AU - Zheng, Pengcheng

AU - Chi, Yonggui Robin

PY - 2019/12/6

Y1 - 2019/12/6

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AB - 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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Carbene-Catalyzed Enantioselective Addition of Thioamides to Bromoenals for Access to Thiazinone Heterocycles

Abstract

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ASJC Scopus Subject Areas

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