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Enantioselective Synthesis of 4‐(Dimethylamino)pyridines through a Chemical Oxidation‐Enzymatic Reduction Sequence. Application in Asymmetric Catalysis
Author(s) -
Busto Eduardo,
GotorFernández Vicente,
Gotor Vicente
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600274
Subject(s) - enantioselective synthesis , chemistry , catalysis , nucleophile , pyridine , organic chemistry , stereoselectivity , optically active , combinatorial chemistry
Enantiomerically pure 4‐(dimethylamino)‐3‐(1‐hydroxyalkyl)pyridines and 4‐(dimethylamino)‐3‐[hydroxy(phenyl)methyl]pyridine have been prepared through efficient chemoenzymatic routes. For this purpose different lipases and oxidoreductases have been tested in the preparation of optically active 4‐chloro derivatives and baker’s yeast was found to be an excellent catalyst for the bioreductions of the corresponding ketones. Their applications as enantioselective nucleophilic catalysts have been studied, important catalytic properties were observed in the stereoselective construction of quaternary centers.