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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.

the journal of organic chemistry

Enantiopure <i>Trans</i>-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1′-DiBoc-2,2′-Biaziridine with Grignard Reagents

Enantiopure Trans-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1′-DiBoc-2,2′-Biaziridine with Grignard Reagents