title: trans-6-Aminocyclohept-3-enols, a new designed polyfunctionalized chiral building block for the asymmetric synthesis of 2-substituted-4-hydroxypiperidines.
abstract: trans-6-Aminocyclohept-3-enols 18 and ent-18 are new designed polyfunctionalized chiral building blocks for piperidine alkaloids synthesis and are prepared in high yields from the enzymatically derived cyclohept-3-ene-1,6-diol monoacetate (-)-8. Efficient highly enantioselective syntheses of cis-4-hydroxypipecolic acid (1) and piperidines 3 and 4, in both enantiomeric forms, are described. [reaction: see text]
authors.affiliation: Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Venezian 21, 20133 Milan, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Celestini
authors.forename: Bruno
authors.initials: B
authors.lastname: Danieli
authors.forename: Giordano
authors.initials: G
authors.lastname: Lesma
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sacchetti
authors.forename: Alessandra
authors.initials: A
authors.lastname: Silvani
authors.forename: Daniele
authors.initials: D
authors.lastname: Passarella
authors.forename: Andrea
authors.initials: A
authors.lastname: Virdis
mesh_terms: D000470:Alkaloids; D003508:Cycloheptanes / Q000138:chemical synthesis*; D019850:Heptanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D008049:Lipase / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D003508:Cycloheptanes; D007202:Indicators and Reagents; D010880:Piperidines; D019850:Heptanol; D008049:Lipase