N-Heterocyclic Carbene-Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality

Tingting Li; Chengli Mou; Puying Qi; Xiaolin Peng; Shichun Jiang; Gefei Hao; Wei Xue; Song Yang; Lin Hao; Yonggui Robin Chi; Zhichao Jin

doi:10.1002/anie.202010606

N-Heterocyclic Carbene-Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality

Tingting Li, Chengli Mou, Puying Qi, Xiaolin Peng, Shichun Jiang, Gefei Hao, Wei Xue, Song Yang, Lin Hao, Yonggui Robin Chi, Zhichao Jin^*

^*Corresponding author for this work

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

94 Citations (Scopus)

Abstract

A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C−N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.

Original language	English
Pages (from-to)	9362-9367
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	17
DOIs	https://doi.org/10.1002/anie.202010606
Publication status	Published - Apr 19 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 Wiley-VCH GmbH

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

atroposelective reaction
chiral C−N axis
N-heterocyclic carbenes
organocatalysis

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10.1002/anie.202010606

Cite this

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title = "N-Heterocyclic Carbene-Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality",

abstract = "A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C−N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.",

keywords = "atroposelective reaction, chiral C−N axis, N-heterocyclic carbenes, organocatalysis",

author = "Tingting Li and Chengli Mou and Puying Qi and Xiaolin Peng and Shichun Jiang and Gefei Hao and Wei Xue and Song Yang and Lin Hao and Chi, {Yonggui Robin} and Zhichao Jin",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

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day = "19",

doi = "10.1002/anie.202010606",

language = "English",

volume = "60",

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journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - N-Heterocyclic Carbene-Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality

AU - Li, Tingting

AU - Mou, Chengli

AU - Qi, Puying

AU - Peng, Xiaolin

AU - Jiang, Shichun

AU - Hao, Gefei

AU - Xue, Wei

AU - Yang, Song

AU - Hao, Lin

AU - Chi, Yonggui Robin

AU - Jin, Zhichao

PY - 2021/4/19

Y1 - 2021/4/19

N2 - A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C−N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.

AB - A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C−N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.

KW - atroposelective reaction

KW - chiral C−N axis

KW - N-heterocyclic carbenes

KW - organocatalysis

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DO - 10.1002/anie.202010606

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C2 - 33527623

AN - SCOPUS:85103032732

SN - 1433-7851

VL - 60

SP - 9362

EP - 9367

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 17

ER -

N-Heterocyclic Carbene-Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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