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)

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