title: α-Lithiation-electrophile trapping of N-thiopivaloylazetidin-3-ol: stereoselective synthesis of 2-substituted 3-hydroxyazetidines.
abstract: α-Lithiation of N-thiopivaloylazetidin-3-ol and subsequent electrophile trapping provides access to a range of 2-substituted 3-hydroxyazetidines with generally good trans-diastereoselectivity, aside from deuteration, which gives the cis-diastereoisomer. Deuterium labeling studies indicate that the initial α-deprotonation occurs preferentially, but not exclusively, in a trans-selective manner. These studies also suggest that the stereochemical outcome of the electrophile trapping depends on the electrophile used but is independent of which α-proton (cis or trans to the hydroxyl group) is initially removed.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, United Kingdom. david.hodgson@chem.ox.ac.uk
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Christopher I
authors.initials: CI
authors.lastname: Pearson
authors.forename: Amber L
authors.initials: AL
authors.lastname: Thompson
mesh_terms: D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D011522:Protons; D013237:Stereoisomerism
chemical_list: D001384:Azetidines; C582647:N-thiopivaloylazetidin-3-ol; D011522:Protons; D008094:Lithium; D003903:Deuterium