title: A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines.
abstract: A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented.
authors.affiliation: Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
authors.forename: Emma M
authors.initials: EM
authors.lastname: Dangerfield
authors.forename: Shivali A
authors.initials: SA
authors.lastname: Gulab
authors.forename: Catherine H
authors.initials: CH
authors.lastname: Plunkett
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
mesh_terms: D000586:Amination; D002219:Carbamates / Q000737:chemistry; D007700:Kinetics; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014993:Xylitol / Q000737:chemistry
chemical_list: D002219:Carbamates; D011759:Pyrrolidines; C032519:pyrrolidine; D014993:Xylitol