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US 8,044,245 B2Granted
Method for the preparation of optically active 2-sulfonyloxy-1-phenylethanol derivatives
AssigneeKorea Research Institute of Chemical Technology
InventorsKee-In Lee, Do-Min Lee
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Abstract
Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an α-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.
Claims3
A method for preparing an optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II), comprising
- i) reacting (pentamethylcyclopentadienyl)rhodium(III) chloride dimer ([Rh(C5Me5)Cl2]2) with optically active 1,2-diphenylethylene-N-(p-toluenesulfonyl)diamine in methylene chloride as a solvent and optionally in the presence of triethylamine, and removing the solvent from the reaction product to obtain a rhodium compound having pentamethylcyclopentadienyl group;
- and
- ii) subjecting an α-sulfonyloxy acetophenone compound to asymmetrical reduction in the presence of the rhodium compound having pentamethylcyclopentadienyl group as a catalyst and a hydrogen donor:
- wherein,
- X is tosyloxy or mesyloxy;
- R is one or more substituents, each independently, selected from the group consisting of H, F, Cl, Br, OH, OMe, OBn, OAc, OTBS, OTs, NH2, NHBn, NHBz, NHTBS, NHMs, N(Ac)2, N(Ms)2, NO2, CF3, Me, tert-Bu and CH2OMe, substituted in the ortho-, metha- or para-position of the phenyl moiety, the substituents being optionally fused together to form a benzene, dioxane or dioxolane ring, wherein Me=methyl, Bn=benzyl, Bu=butyl, Bz=benzoyl, TBS=tert-butyldimethylsilyl, Ms=mesyl, Ac=acetyl, and Ts=tosyl.
3 more elements
Dependencies are inferred from the claim text.