Lewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor-acceptor cyclopropanes: synthesis of gamma-sulfoximino malonic diesters

TitleLewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor-acceptor cyclopropanes: synthesis of gamma-sulfoximino malonic diesters
Publication TypeJournal Article
Year of Publication2022
AuthorsMore, SG, Suryavanshi, G
JournalOrganic & Biomolecular Chemistry
Volume20
Issue12
Pagination2518-2529
Date PublishedMAR
Type of ArticleArticle
ISSN1477-0520
Abstract

Scandium triflate (Sc(OTf)(3)) catalyzed, mild, and regioselective ring-opening reaction of donor-acceptor (D-A) cyclopropanes has been developed using sulfoximines for the synthesis of gamma-sulfoximino malonic diesters. This protocol allows the synthesis of different N-alkyl sulfoximines in good to excellent yields (up to 94%) with broad functional group tolerance. In this process, N-H and C-C bonds are cleaved to form new C-N and C-H bonds. The feasibility of this method is supported by a gram-scale reaction and synthetic elaboration of the obtained product.

DOI10.1039/d2ob00213b
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.890

Divison category: 
Chemical Engineering & Process Development
Database: 
Web of Science (WoS)

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