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Inversion of Optically Active Dihydropyridines by Oxidation and Electroreduction
Author(s) -
Straub Alexander,
Goehrt Axel
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199626621
Subject(s) - optically active , inversion (geology) , cathodic protection , stereoselectivity , chemistry , combinatorial chemistry , walden inversion , stereochemistry , electrochemistry , organic chemistry , catalysis , electrode , geology , paleontology , structural basin
Stereoselective oxidation of optically active dihydropyridines with NOBF 4 or MnO 2 leads with either inversion or retention to axial chiral arylpyridines (see below), which can be converted by cathodic reduction into the corresponding dihydropyridines. This is the first report of the successful inversion of configuration or dihydropyridines.