Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines

Fuhao Zhang; Xuan Dai; Lei Dai; Wenrui Zheng; Wai Lun Chan; Xiaodong Tang; Xumu Zhang; Yixin Lu

doi:10.1002/anie.202203212

Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines

Fuhao Zhang, Xuan Dai, Lei Dai, Wenrui Zheng, Wai Lun Chan, Xiaodong Tang, Xumu Zhang, Yixin Lu

Research output: Journal article publication › Journal article › Academic research › peer-review

33 Citations (Scopus)

Abstract

A phosphine-catalyzed highly enantioselective and diastereoselective (up to 98 % ee and >20 : 1 dr) (3+2) annulation between vinylcyclopropanes and N-tosylaldimines has been developed, which allows facile access to a range of highly functionalized chiral pyrrolidines. Notably, this method makes use of vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation reaction, which will offer new opportunities for potential applications of cyclopropanes substrates in phosphine-catalyzed organic transformations.

Original language	English
Article number	e202203212
Journal	Angewandte Chemie - International Edition
Volume	61
Issue number	24
DOIs	https://doi.org/10.1002/anie.202203212
Publication status	Published - 13 Jun 2022
Externally published	Yes

Keywords

Annulation
Enantioselective
Phosphine Catalysis
Pyrrolidines
Vinylcyclopropanes

ASJC Scopus subject areas

Catalysis
General Chemistry

More information

10.1002/anie.202203212

Cite this

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title = "Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines",

abstract = "A phosphine-catalyzed highly enantioselective and diastereoselective (up to 98 % ee and >20 : 1 dr) (3+2) annulation between vinylcyclopropanes and N-tosylaldimines has been developed, which allows facile access to a range of highly functionalized chiral pyrrolidines. Notably, this method makes use of vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation reaction, which will offer new opportunities for potential applications of cyclopropanes substrates in phosphine-catalyzed organic transformations.",

keywords = "Annulation, Enantioselective, Phosphine Catalysis, Pyrrolidines, Vinylcyclopropanes",

author = "Fuhao Zhang and Xuan Dai and Lei Dai and Wenrui Zheng and Chan, {Wai Lun} and Xiaodong Tang and Xumu Zhang and Yixin Lu",

note = "Funding Information: Y.L. thanks the Singapore National Research Foundation, Prime Minister's Office for the NRF Investigatorship Award (A‐0004067‐00‐02). Financial support from the Ministry of Education of Singapore (A‐0008481‐00‐00) is also acknowledged. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jun,

day = "13",

doi = "10.1002/anie.202203212",

language = "English",

volume = "61",

journal = "Angewandte Chemie - International Edition",

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AU - Zhang, Fuhao

AU - Dai, Xuan

AU - Dai, Lei

AU - Zheng, Wenrui

AU - Chan, Wai Lun

AU - Tang, Xiaodong

AU - Zhang, Xumu

AU - Lu, Yixin

N1 - Funding Information: Y.L. thanks the Singapore National Research Foundation, Prime Minister's Office for the NRF Investigatorship Award (A‐0004067‐00‐02). Financial support from the Ministry of Education of Singapore (A‐0008481‐00‐00) is also acknowledged. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/6/13

Y1 - 2022/6/13

N2 - A phosphine-catalyzed highly enantioselective and diastereoselective (up to 98 % ee and >20 : 1 dr) (3+2) annulation between vinylcyclopropanes and N-tosylaldimines has been developed, which allows facile access to a range of highly functionalized chiral pyrrolidines. Notably, this method makes use of vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation reaction, which will offer new opportunities for potential applications of cyclopropanes substrates in phosphine-catalyzed organic transformations.

AB - A phosphine-catalyzed highly enantioselective and diastereoselective (up to 98 % ee and >20 : 1 dr) (3+2) annulation between vinylcyclopropanes and N-tosylaldimines has been developed, which allows facile access to a range of highly functionalized chiral pyrrolidines. Notably, this method makes use of vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation reaction, which will offer new opportunities for potential applications of cyclopropanes substrates in phosphine-catalyzed organic transformations.

KW - Annulation

KW - Enantioselective

KW - Phosphine Catalysis

KW - Pyrrolidines

KW - Vinylcyclopropanes

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U2 - 10.1002/anie.202203212

DO - 10.1002/anie.202203212

M3 - Journal article

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AN - SCOPUS:85128282470

SN - 1433-7851

VL - 61

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines

Abstract

Keywords

ASJC Scopus subject areas

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