title: Asymmetric synthesis of acyclic 1,3-amino alcohols by reduction of N-sulfinyl beta-amino ketones. Formal synthesis of (-)-pinidinol and (+)- epipinidinol.
abstract: Stereoselective reduction of acyclic N-sulfinyl beta-amino ketones with (LiEt(3)BH) and Li(t-BuO)(3)AlH, respectively, gave anti- and syn-1,3-amino alcohols with excellent selectivity. A formal asymmetric synthesis of the hydroxy piperidine alkaloids (-)-pinidinol and (+)-epipinidinol from a common N-sulfinyl beta-amino ketone ketal precursor was developed. The pinidinol piperidine ring was formed via a novel acid-catalyzed cascade reaction of a N-sulfinylamino silyl protected alcohol ketal.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19096, USA. fdavis@temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: Paul M
authors.initials: PM
authors.lastname: Gaspari
authors.forename: Brad M
authors.initials: BM
authors.lastname: Nolt
authors.forename: Peng
authors.initials: P
authors.lastname: Xu
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D007202:Indicators and Reagents; D007659:Ketones; D010880:Piperidines; C431206:pinidinol