Efficient Synthesis of Optically Pure 1,1,1-Trifluoro-2-alkanols through Lipase-Catalyzed Acylation in Organic Media

作者: Hiroki Hamada , Mizuho Shiromoto , Makoto Funahashi , Toshiyuki Itoh , Kaoru Nakamura

DOI: 10.1021/JO951976A

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摘要: Lipase-catalyzed esterification was successfully utilized for the optical resolution of 1,1,1-trifluoro-2-alkanol 1 when racemic treated with lipase from Candida antarctica in hexane presence molecular sieves (4 A) to provide corresponding (S)-acetate 2 an optically pure state. Alkanol is known as important component liquid crystal compounds which display remarkable ferroelectric (FLC) characteristics. Five types alkanols, i.e., 1,1,1-trifluoro-2-octanol (1a), 1,1,1-trifluoro-2-nonanol (1b), 1,1,1-trifluoro-2-decanol (1c), 1,1,1-trifluoro-2-undecanol (1d), and 1,1,1-trifluoro-8-(benzyloxy)-2-octanol (1e), were thus obtained by lipase-catalyzed acylation.

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