Felluga Fulvia, Baratta Walter, Fanfoni Lidia, Pitacco Giuliana, Rigo Pierluigi, Benedetti Fabio
Dipartimento di Scienze Chimiche, Università di Trieste, via Giorgieri 1, I-34127 Trieste, Italy.
J Org Chem. 2009 May 1;74(9):3547-50. doi: 10.1021/jo900271x.
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.
基于6-苯基-2-氨基甲基吡啶和2-氨基甲基苯并[h]喹啉骨架的手性、非外消旋钳形配体，是通过一种化学酶法从2-吡啶基乙酮和2-苯并喹啉基乙酮出发制得的。在对映体区分步骤中，通过面包酵母还原酮以及脂肪酶介导的外消旋醇的动态动力学拆分，得到了绝对构型相反的仲醇。它们转化为同手性的1-甲基-1-杂芳基乙胺时，光学纯度没有损失，从而得到了用于对映选择性催化的钳形配体。
