Uenishi, Jun'ichi Hiraoka, Takao Hata, Shinichiro Nishiwaki, Kenji Yonemitsu, Osamu Nakamura, Kaoru Tsukube, Hiroshi Chiral Pyridines:  Optical Resolution of 1-(2-Pyridyl)- and 1-[6-(2,2‘-Bipyridyl)]ethanols by Lipase-Catalyzed Enantioselective Acetylation The resolution of racemic 1-(2-pyridyl)ethanols <b>2a</b>−<b>n</b>, including the 2,2‘-bipyridyl and isoquinolyl derivatives, by lipase-catalyzed asymmetric acetylation with vinyl acetate is reported. The reactions were carried out in diisopropyl ether at either room temperature or 60 °C using <i>Candida antarctica</i> lipase (CAL) to give (<i>R</i>)-acetate and unreacted (<i>S</i>)-alcohol with excellent enantiomeric purities in good yields. The reaction rate was relatively slow at room temperature for substrates bearing an sp<sup>3</sup>-type carbon at the 6-position on the pyridine ring, such as <b>2c</b>, <b>2d</b>, and <b>2e</b>, and for those bearing 1-hydroxypropyl and allyl groups at the 2-position on the pyridine ring, such as <b>2l</b> and <b>2m</b>. In such cases, a higher temperature was required. Thus, when the reaction was conducted at 60 °C, it was accelerated 3- to 7-fold without losing the high enantiospecificity. However, the reaction of homoallylic alcohol <b>2n</b> was not complete, even when the reaction was continued for a longer period of time at 60 °C. This enzymatic resolution can be used practically in a wide range of reaction scales from 10 mg to 10 g or more. This catalyst can be used repeatedly with a 5−10% loss of the initial activity with each use. homoallylic alcohol 2 n;pyridine ring;CAL;Candida antarctica lipase;room temperature 1998-03-24
    https://acs.figshare.com/articles/journal_contribution/Chiral_Pyridines_Optical_Resolution_of_1-_2-Pyridyl_-_and_1-_6-_2_2_-Bipyridyl_ethanols_by_Lipase-Catalyzed_Enantioselective_Acetylation/3708003
10.1021/jo971521g.s002