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Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. © 2009 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tet.2009.09.104

Type

Journal article

Journal

Tetrahedron

Publication Date

05/12/2009

Volume

65

Pages

10192 - 10213