Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides

Yan Lin; Qijun Wang; Yang Wu; Chang Wang; Hao Jia; Cheng Zhang; Jiaxing Huang; Hongchao Guo

doi:10.1039/C8RA08881K

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Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides†

Yan Lin,^a Qijun Wang,^a Yang Wu,^a Chang Wang,^a Hao Jia,^a Cheng Zhang,

^a Jiaxing Huang*^a and Hongchao Guo

*^a

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* Corresponding authors

^a Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
E-mail: hchguo@cau.edu.cn, 05084@cau.edu.cn

Abstract

The palladium-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and 1-azadienes has been developed under mild reaction conditions, giving the multisubstituted cyclopentane derivatives in good to excellent yields with moderate to good diastereoselectivities. The relative configuration of both diastereomers of the products have been determined through X-ray crystallographic diffraction.

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DOI: https://doi.org/10.1039/C8RA08881K
Article type: Paper
Submitted: 26 Oct 2018
Accepted: 29 Nov 2018
First published: 05 Dec 2018
This article is Open Access

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RSC Adv., 2018,8, 40798-40803

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Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides

Y. Lin, Q. Wang, Y. Wu, C. Wang, H. Jia, C. Zhang, J. Huang and H. Guo, RSC Adv., 2018, 8, 40798 DOI: 10.1039/C8RA08881K

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Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides†

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Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides

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