環隣接位に不斉中心を有する光学活性ピリジン類の合成 [in Japanese] Synthesis of Optically Active Pyridines with a Chiral Center at the Next Position to the Ring [in Japanese]
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Chiral compounds containing a pyridine unit have been used widely for many functional molecules including ligands for molecular recognition chemistry and catalytic asymmetric reactions and medicines. In this review, the synthesis of chiral non-racemic pyridinylethyl units and some functional molecules that have the units are described. Our synthetic approach involves a lipase catalyzed acetylation of pyridinyl alcohols and a stereospecific subsitution of their methane-sulfonates with <I>N</I>-, <I>S</I>-, <I>O</I>-, and <I>C</I>-nucleophiles. Although a nucleophilic substitution reaction on the benzylic position has been extensively investigated, there have been few studies of that on the pyridinylmethyl position. We have revealed that perfect stereospecific substitutions occur in the reaction of non-racemic 1- (2-pyridinyl) ethyl methanesulfonates with various nucleophiles through a S<I>N</I>2 process. A number of optically pure chiral non-racemic 1- (2-pyridinyl) ethyl derivatives were synthesized.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 65(2), 127-138, 2007-02-01
The Society of Synthetic Organic Chemistry, Japan