title: Highly enantio- and diastereoselective tandem generation of cyclopropyl alcohols with up to four contiguous stereocenters.
abstract: Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropyl alcohols with up to four contiguous stereocenters are reported. Route 1 involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective cyclopropanation. Route 2 parallels route 1, except that iodoform is used to generate the zinc carbenoid, and the products are iodocyclopropyl alcohols. Route 3 entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective cyclopropanation.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Hun Young
authors.initials: HY
authors.lastname: Kim
authors.forename: Alice E
authors.initials: AE
authors.lastname: Lurain
authors.forename: Patricia
authors.initials: P
authors.lastname: García-García
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000438:Alcohols