title: Flexible, phase-transfer catalyzed approaches to 4-substituted prolines.
abstract: A range of 4-substituted prolines can be rapidly synthesized from a protected glycine Schiff base in only four steps and in 27-55% overall yield. Phase transfer catalysis allows direct access to both enantiomeric series, and the relative stereochemistry at the 4-position is readily controlled (>10:1 dr) through the choice of hydrogenation conditions.
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh , West Mains Road, Edinburgh, EH9 3JJ, U.K.
authors.forename: Heather J
authors.initials: HJ
authors.lastname: Johnston
authors.forename: Fergus S
authors.initials: FS
authors.lastname: McWhinnie
authors.forename: Felicetta
authors.initials: F
authors.lastname: Landi
authors.forename: Alison N
authors.initials: AN
authors.lastname: Hulme
mesh_terms: D002384:Catalysis; D005998:Glycine / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure; D009842:Oligopeptides / Q000494:pharmacology; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012545:Schiff Bases; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides; D012545:Schiff Bases; C545819:bisebromoamide; D011392:Proline; D005998:Glycine