Issue 16, 2021
From the journal:

Organic & Biomolecular Chemistry

Organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of isocyanoacetates with saccharin-derived 1-azadienes†

Li Chang,a   Guang-Yu Zhu,a   Ting Yang,a   Xiao-Li Zhao, ORCID logo b   Min Shiac  and  Mei-Xin Zhao ORCID logo *a  

* Corresponding authors

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, China
E-mail: mxzhao@ecust.edu.cn

b Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China

Abstract

An efficient organocatalytic diastereo- and enantioselective formal [3 + 2] cycloaddition reaction of α-isocyanoacetates with saccharin-derived 1-azadienes catalyzed by a dihydroquinine derived squaramide catalyst has been investigated, and it furnished the corresponding directly linked benzo[d]isothiazole 1,1-dioxide-dihydropyrroles with two adjacent tertiary-quaternary stereocenters in high yields (up to 98%), with moderate to excellent stereoselectivities (up to >20 : 1 dr and 97% ee) under mild conditions.

Graphical abstract: Organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of isocyanoacetates with saccharin-derived 1-azadienes

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Article information

DOI
https://doi.org/10.1039/D1OB00115A
Article type
Paper
Submitted
22 Jan 2021
Accepted
23 Mar 2021
First published
25 Mar 2021

Org. Biomol. Chem., 2021,19, 3687-3697

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Organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of isocyanoacetates with saccharin-derived 1-azadienes

L. Chang, G. Zhu, T. Yang, X. Zhao, M. Shi and M. Zhao, Org. Biomol. Chem., 2021, 19, 3687 DOI: 10.1039/D1OB00115A

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