Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives

摘要

2-Aza-1,3-dienes 1 which are readily prepared from carboxylic acids cycloadd to aldehydes to give good yields of 1,3-oxazinones 3. The cycloadditions were highly diastereoselective in favour of the endo adducts. Hydrolysis of 1,3-oxazinones 3 stereoselectively yielded the corresponding beta-hydroxyamides 4. (C) 1999 Published by Elsevier Science Ltd. All rights reserved. [References: 9]