Enantiopure Trans-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1'-DiBoc-2,2'-Biaziridine with Grignard Reagents.
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.
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
Matthew D
MD
Kennedy
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
Stephen J
SJ
Bailey
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
Steven M
SM
Wales
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
Paul A
PA
Keller