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

Authors

Matthew David Kennedy, University of WollongongFollow
Stephen Bailey, University of WollongongFollow
Steven M. Wales, University of WollongongFollow
Paul A. Keller, University of WollongongFollow

RIS ID

101409

Publication Details

Kennedy, M. D., Bailey, S. J., Wales, S. M. & Keller, P. A. (2015). Enantiopure trans -4,5-disubstituted 2-imidazolidinones via copper(I)-catalyzed ring opening of 1,1′-DiBoc-2,2′-biaziridine with Grignard reagents. Journal of Organic Chemistry, 80 (11), 5992-5998.

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.