Asymmetric Synthesis of cis-Aminocyclopentenols, Building Blocks for Medicinal Chemistry
journal contributionposted on 07.02.2014, 00:00 by Ahmed M. Zaed, Mark W. Grafton, Sajjad Ahmad, Andrew Sutherland
A highly efficient one-pot multistep process involving an asymmetric Pd(II)-catalyzed Overman rearrangement and a Ru(II)-catalyzed ring-closing metathesis reaction has been developed for the preparation of (R)- or (S)-aminocyclopenta-2-enes. The rapid strategy employed and the relatively mild conditions of the one-pot process allowed the multigram synthesis of the carbocycles in high enantiomeric excess (92% ee). The synthetic utility of these compounds was demonstrated by the stereoselective incorporation of hydroxyl groups, generating cis-4- and cis-5-aminocyclopenta-2-en-1-ols, important building blocks for medicinal chemistry.