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Influence of A 1,3 Strain on the Stereochemical Outcome of Acid‐Mediated Amido Cyclization in the Synthesis of 2‐(4‐Methoxyphenyl)‐3,4‐(dihydroxy)piperidines
Author(s) -
Ramakrishna Katakam,
Jagadeesh Yerri,
Ramakrishna K. V. S,
Rao Joshi Laxmikanth,
Rao Batchu Venkateswara
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501577
Subject(s) - chemistry , strain (injury) , allylic rearrangement , stereochemistry , group (periodic table) , medicinal chemistry , organic chemistry , catalysis , medicine
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 (A 1,3 strain) than by the participation of a neighboring group.