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

Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
28 Apr 2021
Historique:
entrez: 28 4 2021
pubmed: 29 4 2021
medline: 29 4 2021
Statut: ppublish

Résumé

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.

Identifiants

DOI: 10.1039/d1ob00115a PMID: 33908569
pubmed: 33908569
doi: 10.1039/d1ob00115a
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

3687-3697

Auteurs

Li Chang (L)

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. mxzhao@ecust.edu.cn.

Guang-Yu Zhu (GY)

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. mxzhao@ecust.edu.cn.

Ting Yang (T)

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. mxzhao@ecust.edu.cn.

Xiao-Li Zhao (XL)

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.
ORCID: 0000-0002-4458-6432

Min Shi (M)

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. mxzhao@ecust.edu.cn and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

Mei-Xin Zhao (MX)

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. mxzhao@ecust.edu.cn.
ORCID: 0000-0001-9182-8214

Classifications MeSH