title: Asymmetric synthesis of 3-hydroxy-pyrrolidines via tin-lithium exchange and cyclization.
abstract: We report a method for the synthesis of chiral pyrrolidines using tin-lithium exchange and cyclization reactions. The precursors are formed readily from simple starting materials and undergo tin-lithium exchange by treatment with n-butyllithium. Subsequent intramolecular carbolithiation is stereoselective to give highly enantiomerically enriched pyrrolidines in excellent yields.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany.
authors.forename: Guido
authors.initials: G
authors.lastname: Christoph
authors.forename: Christian
authors.initials: C
authors.lastname: Stratmann
authors.forename: Iain
authors.initials: I
authors.lastname: Coldham
authors.forename: Dieter
authors.initials: D
authors.lastname: Hoppe
mesh_terms: D003500:Cyclization; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
chemical_list: D011759:Pyrrolidines; D014001:Tin; D008094:Lithium