title: Access to 2,6-disubstituted piperidines: control of the diastereoselectivity, scope, and limitations. Applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D.
abstract: Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β'-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.
authors: Clermont Université, ENSCCF, Institut de Chimie de Clermont-Ferrand (ICCF), BP 10448F-63000, Clermont-Ferrand, France.
authors: Isabelle
authors: I
authors: Abrunhosa-Thomas
authors: Aurélie
authors: A
authors: Plas
authors: Alexandre
authors: A
authors: Vogrig
authors: Nishanth
authors: N
authors: Kandepedu
authors: Pierre
authors: P
authors: Chalard
authors: Yves
authors: Y
authors: Troin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007659:Ketones; D010880:Piperidines; C002351:Solenopsin A