Highly enantio- and diastereoselective one-pot synthesis of acyclic epoxy alcohols with three contiguous stereocenters.
Two highly enantio- and diastereoselective one-pot procedures for the synthesis of epoxy alcohols with up to three contiguous stereocenters are reported. Route one involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective epoxidation. Route two entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective epoxidation. The oxidant for the epoxidation is generated by exposure of the allylic alkoxide intermediate and the remaining organozinc reagent to dioxygen. Upon addition of catalytic titanium tetraisopropoxide, the directed epoxidation yields the epoxy alcohols with good to excellent yields.
Lurain
Alice E
AE
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Maestri
Aaron
A
Kelly
Ann Rowley
AR
Carroll
Patrick J
PJ
Walsh
Patrick J
PJ
D000438:Alcohols / Q000138:chemical synthesis*; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000438:Alcohols; D004852:Epoxy Compounds