Highly enantio- and diastereoselective tandem generation of cyclopropyl alcohols with up to four contiguous stereocenters.
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.
Kim
Hun Young
HY
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Lurain
Alice E
AE
García-García
Patricia
P
Carroll
Patrick J
PJ
Walsh
Patrick J
PJ
D000438:Alcohols / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000438:Alcohols