title: Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry.
abstract: 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.
authors.forename: Ahmed M
authors.initials: AM
authors.lastname: Zaed
authors.forename: Mark W
authors.initials: MW
authors.lastname: Grafton
authors.forename: Sajjad
authors.initials: S
authors.lastname: Ahmad
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D002626:Chemistry, Pharmaceutical; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; C520587:aminocyclopentenol; D010165:Palladium; D012428:Ruthenium