Tetrahedron Letters

Diastereoselective synthesis of trisubstituted piperidines: a versatile synthon for elaboration of uncommon poly (aza) heterocyclic structures

A Plas, I Abrunhosa-Thomas, P Chalard, Y Troin

Index: Plas, Aurelie; Abrunhosa-Thomas, Isabelle; Chalard, Pierre; Troin, Yves Tetrahedron Letters, 2011 , vol. 52, # 51 p. 6873 - 6876

Full Text: HTML

Citation Number: 4

Abstract

Hetero Michael addition on chiral β′-amino-α, β-unsaturated ketone furnished, after some structural modifications, β, β′-diaminoketals. Mannich type reaction of these diamines with an aldehyde led, with a high diastereoselectivity, to trisubstituted piperidines. Starting from a functionalized aldehyde and after subsequent deprotection of the amino group, an intramolecular Michael addition provided octahydro-2H-pyrrolo-[3, 4-b]-pyridine, an ...