title: Oxazolidine synthesis by complementary stereospecific and stereoconvergent methods.
abstract: Complementary stereospecific and stereoconvergent reactions for enantioselective synthesis of 1,3-oxazolidines are reported. In the presence of a rhodium catalyst, reaction of enantioenriched butadiene monoxide with aryl imines is stereospecific (99% ee). Alternatively, the reaction of racemic butadiene monoxide, in the presence of a chiral palladium or nickel catalyst, provides an enantioselective synthesis of 1,3-oxazolidines (up to 94% ee). Synthesis of either the cis- or trans-1,3-oxazolidines is also accomplished under catalyst control.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
authors.forename: Michael B
authors.initials: MB
authors.lastname: Shaghafi
authors.forename: Robin E
authors.initials: RE
authors.lastname: Grote
authors.forename: Elizabeth R
authors.initials: ER
authors.lastname: Jarvo
mesh_terms: D002384:Catalysis; D007700:Kinetics; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D010080:Oxazoles; C064210:oxazolidine