Parallel copper catalysis: Diastereoselective synthesis of polyfunctionalized azetidin-2-imines

Yanpeng Xing; Hongyang Zhao; Qiongyi Shang; Jing Wang; Ping Lu; Yanguang Wang

doi:10.1021/ol4010323

Parallel copper catalysis: Diastereoselective synthesis of polyfunctionalized azetidin-2-imines

Yanpeng Xing, Hongyang Zhao, Qiongyi Shang, Jing Wang, Ping Lu^*, Yanguang Wang

^*Corresponding author for this work

Zhejiang University

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

36 Citations (Scopus)

Abstract

An efficient and diastereoselective synthesis of highly functionalized azetidin-2-imines has been achieved through a parallel catalysis strategy, including a copper-catalyzed azide-alkyne cycloaddition, a copper-catalyzed C_sp-Csp² cross-coupling reaction, and an intermolecular [2 + 2] cycloaddition. The products could be conveniently converted into the structurally interesting dihydroazeto[1,2-a]benzo[e]azepin-2(4H)-imines.

Original language	English
Pages (from-to)	2668-2671
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	11
DOIs	https://doi.org/10.1021/ol4010323
Publication status	Published - 7 Jun 2013
Externally published	Yes

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title = "Parallel copper catalysis: Diastereoselective synthesis of polyfunctionalized azetidin-2-imines",

abstract = "An efficient and diastereoselective synthesis of highly functionalized azetidin-2-imines has been achieved through a parallel catalysis strategy, including a copper-catalyzed azide-alkyne cycloaddition, a copper-catalyzed Csp-Csp2 cross-coupling reaction, and an intermolecular [2 + 2] cycloaddition. The products could be conveniently converted into the structurally interesting dihydroazeto[1,2-a]benzo[e]azepin-2(4H)-imines.",

author = "Yanpeng Xing and Hongyang Zhao and Qiongyi Shang and Jing Wang and Ping Lu and Yanguang Wang",

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T1 - Parallel copper catalysis

T2 - Diastereoselective synthesis of polyfunctionalized azetidin-2-imines

AU - Xing, Yanpeng

AU - Zhao, Hongyang

AU - Shang, Qiongyi

AU - Wang, Jing

AU - Lu, Ping

AU - Wang, Yanguang

PY - 2013/6/7

Y1 - 2013/6/7

N2 - An efficient and diastereoselective synthesis of highly functionalized azetidin-2-imines has been achieved through a parallel catalysis strategy, including a copper-catalyzed azide-alkyne cycloaddition, a copper-catalyzed Csp-Csp2 cross-coupling reaction, and an intermolecular [2 + 2] cycloaddition. The products could be conveniently converted into the structurally interesting dihydroazeto[1,2-a]benzo[e]azepin-2(4H)-imines.

AB - An efficient and diastereoselective synthesis of highly functionalized azetidin-2-imines has been achieved through a parallel catalysis strategy, including a copper-catalyzed azide-alkyne cycloaddition, a copper-catalyzed Csp-Csp2 cross-coupling reaction, and an intermolecular [2 + 2] cycloaddition. The products could be conveniently converted into the structurally interesting dihydroazeto[1,2-a]benzo[e]azepin-2(4H)-imines.

UR - http://www.scopus.com/inward/record.url?scp=84879205734&partnerID=8YFLogxK

U2 - 10.1021/ol4010323

DO - 10.1021/ol4010323

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SP - 2668

EP - 2671

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Parallel copper catalysis: Diastereoselective synthesis of polyfunctionalized azetidin-2-imines

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