Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts 英文参考文献.docVIP

Molecules 2009, 14, 4275-4283; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts ? Mireia Oromí-Farrús 1, Jordi Eras 1, Núria Sala 2, Mercè Torres 2,* and Ramon Canela 1,* 1 Chemistry Department, Lleida University, 25198-Lleida, Spain; E-Mails: mireia.oromi@quimica.udl.cat (M.O-F.); eras@quimica.udl.cat (J.E.) 2 Food Technology Department, Lleida University, 25198-Lleida, Spain; E-Mail: nsala@tecal.udl.cat (N.S.) ? This paper is taken in part from the Ph.D. thesis of Mireia Oromí-Farrús. * Authors to whom correspondence should be addressed: E-Mails: canela@quimica.udl.cat (R.C.); mtorres@tecal.udl.cat (M.T.) Received: 31 August 2009; in revised form: 26 September 2009 / Accepted: 16 October 2009 / Published: 23 October 2009 Abstract: Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida antarctica (Novozym? 435), Rhizomucor miehei (Lipozyme IM), and “resting cells” from a Rhizopus oryzae strain that was not mycotoxigenic. The influence of the enzyme and the reaction medium on the selective hydrolysis of isomeric mixtures of halohydrin esters is described. Novozym? 435 allowed preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol after 1–3 h of reaction at 40 °C in [BMIM][PF6]. Keywords: (S)-1-bromomethyl-1-heptanol; (S)-1-chloromethyl-1-heptanol; lipases; enzymatic resolution  Molecules 2009, 14 4276 1. Introduction Racemic halohydrins and haloesters can be obtained using diverse approaches [1]. Among them, our research group has developed a direct methodology for halohydrin ester formation using ionic liquids (I