beta-amino acids to piperidinones by petasis methylenation and acid-induced cyclization

Adriaenssens, L. V. and Hartley, R. C. (2007) beta-amino acids to piperidinones by petasis methylenation and acid-induced cyclization. Journal of Organic Chemistry, 72(26), pp. 10287-10290. (doi:10.1021/jo7019948)

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Abstract

[GRAPHICS] Ester-imine derivatives of beta-amino acids were methylenated with dimethyltitanocene under microwave irradiation and the resulting enol ethers cyclized with Bronsted acid or triisopropylaluminium to give 2,6-syn-disubstituted piperidinones in good yield and diastereoselectivity. The method is analogous to the Petasis-Ferrier rearrangement of 1,3dioxan-4-ones to give tetrahydropyranones.

Item Type:Articles
Keywords:Acid, Acids, Alkylidenation, Asymmetric-Synthesis, Carbonyl Groups, Construction, Cyclization, Derivatives, Diastereoselective Synthesis, Dimethyltitanocene, Drug Discovery, Enol, Ethers, Olefinations, Rearrangement, Substituted Piperidines
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Hartley, Professor Richard
Authors: Adriaenssens, L. V., and Hartley, R. C.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
ISSN:0022-3263

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