Web Release Date: November 14,
-Amino Acids to Piperidinones by Petasis
Methylenation and Acid-Induced Cyclization
WestCHEM Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom richh@chem.gla.ac.uk
Received September 11, 2007
Abstract:
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-amino acids were methylenated
with dimethyltitanocene under microwave irradiation and the
resulting enol ethers cyclized with Brönsted 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 1,3-dioxan-4-ones to give tetrahydropyranones.
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