Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides

Sen Zhang; Zhang-Hong Luo; Wen-Tao Wang; Linghui Qian; Jia-Yu Liao

doi:10.1021/acs.orglett.2c01761

Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides

Sen Zhang
, Zhang-Hong Luo
, Wen-Tao Wang
, Linghui Qian^*
, Jia-Yu Liao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

30 Citations (Scopus)

Abstract

Herein, we report an unprecedented strategy for the simultaneous construction of a remote C–N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C–N atropisomers with the use of activated isocyanides.

Original language	English
Pages (from-to)	4645–4649
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	25
Early online date	20 Jun 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c01761
Publication status	Published - 1 Jul 2022

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10.1021/acs.orglett.2c01761

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title = "Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides",

abstract = "Herein, we report an unprecedented strategy for the simultaneous construction of a remote C–N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C–N atropisomers with the use of activated isocyanides.",

author = "Sen Zhang and Zhang-Hong Luo and Wen-Tao Wang and Linghui Qian and Jia-Yu Liao",

note = "We acknowledge financial support from the National Natural Science Foundation of China (81903574) and the Joint Funds of the Zhejiang Provincial Natural Science Foundation of China (LTZ22B020001). Publisher Copyright: {\textcopyright} 2022 American Chemical Society",

year = "2022",

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doi = "10.1021/acs.orglett.2c01761",

language = "English",

volume = "24",

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journal = "Organic Letters",

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Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides. / Zhang, Sen; Luo, Zhang-Hong; Wang, Wen-Tao et al.
In: Organic Letters, Vol. 24, No. 25, 01.07.2022, p. 4645–4649.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides

AU - Zhang, Sen

AU - Luo, Zhang-Hong

AU - Wang, Wen-Tao

AU - Qian, Linghui

AU - Liao, Jia-Yu

N1 - We acknowledge financial support from the National Natural Science Foundation of China (81903574) and the Joint Funds of the Zhejiang Provincial Natural Science Foundation of China (LTZ22B020001). Publisher Copyright: © 2022 American Chemical Society

PY - 2022/7/1

Y1 - 2022/7/1

N2 - Herein, we report an unprecedented strategy for the simultaneous construction of a remote C–N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C–N atropisomers with the use of activated isocyanides.

AB - Herein, we report an unprecedented strategy for the simultaneous construction of a remote C–N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C–N atropisomers with the use of activated isocyanides.

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.2c01761

U2 - 10.1021/acs.orglett.2c01761

DO - 10.1021/acs.orglett.2c01761

M3 - Journal article

SN - 1523-7060

VL - 24

SP - 4645

EP - 4649

JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

Simultaneous Construction of C–N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides

Abstract

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