Enantiopure trans -4,5-disubstituted 2-imidazolidinones via copper(I)-catalyzed ring opening of 1,1′-DiBoc-2,2′-biaziridine with grignard reagents

Matthew D. Kennedy, Stephen J. Bailey, Steven M. Wales, Paul A. Keller*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

6 Citations (Scopus)

Abstract

The copper-catalyzed ring opening of chiral-pool-derived 1,1′-diBoc-2,2′-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C-C bond constructions concurrent to imidazolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.

Original languageEnglish
Pages (from-to)5992-5998
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number11
DOIs
Publication statusPublished - 5 Jun 2015

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