Katakam Ramakrishna, Y. Jagadeesh, K. Ramakrishna
Feb 19, 2016
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0
Influential Citations
2
Citations
Journal
European Journal of Organic Chemistry
Abstract
The synthesis of 2-(4-methoxyphenyl)-3,4-(dihydroxy)piperidines was accomplished by using ethyl p-methoxycinnamate as the starting material and an acid-mediated amido cyclization reaction as the key step. This short and straightforward strategy avoids extra steps to create the chiral center and does not require a leaving group at the benzylic carbon. This study also showed that the stereochemical outcome of the cyclization reaction is influenced more by allylic 1,3-strain (A1,3 strain) than by the participation of a neighboring group.