Efficient chemoenzymatic synthesis of chiral pincer ligands.
Chiral, nonracemic pincer ligands based on the 6-phenyl-2-aminomethylpyridine and 2-aminomethylbenzo[h]quinoline scaffolds were obtained by a chemoenzymatic approach starting from 2-pyridyl and 2-benzoquinolyl ethanone. In the enantiodifferentiating step, secondary alcohols of opposite absolute configuration were obtained by a baker's yeast reduction of the ketones and by lipase-mediated dynamic kinetic resolution of the racemic alcohols. Their transformation into homochiral 1-methyl-1-heteroarylethanamines occurred without loss of optical purity, giving access to pincer ligands used in enantioselective catalysis.
Felluga
Fulvia
F
Dipartimento di Scienze Chimiche, Università di Trieste, via Giorgieri 1, I-34127 Trieste, Italy. ffelluga@units.it
Baratta
Walter
W
Fanfoni
Lidia
L
Pitacco
Giuliana
G
Rigo
Pierluigi
P
Benedetti
Fabio
F