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    Preparation of 3,3-diphenyl-2,3-epoxy-propionate esters from 3-phenyl-cinnamic acid esters, using method which is suitable for industrial scaling and gives high enantiomeric purity
    46.
    发明专利
    Preparation of 3,3-diphenyl-2,3-epoxy-propionate esters from 3-phenyl-cinnamic acid esters, using method which is suitable for industrial scaling and gives high enantiomeric purity 未知

    公开(公告)号：DE10002393A1

    公开(公告)日：2001-07-26

    申请号：DE10002393

    申请日：2000-01-20

    Applicant: BASF AG

    Inventor： JANSEN ROLF

    IPC: C07D301/03 ,  C07B61/00 ,  C07C69/732 ,  C07D303/48 ,  C07D301/02 ,  C07B53/00

    Abstract: Enantiomerically pure 3,3-diphenyl-2,3-epoxy-propionic acid esters of formula (I) are prepared by: (1) dihydroxylation of a 3-phenyl-cinnamic acid ester of formula (II) by a Sharpless oxidation method (2) selective conversion of the 2-hydroxy group in the resulting compound (III) to a leaving group; and (3) reaction of this leaving group with the 3-hydroxy group to give (I). Enantioselective preparation of 3,3-diphenyl-2,3- epoxy-propionic acid esters of formula (I) comprises: (1) dihydroxylation of a 3-phenyl-cinnamic acid ester of formula (II) by osmium (VIII) oxide catalysis, in the presence of a Sharpless ligand and an oxidizing agent, to give a dihydroxy ester of formula (III); (2) selective conversion of the hydroxy group in the 2-position of (III) to a leaving group; and (3) intramolecular substitution of this leaving group with the hydroxy group in the 3-position of (III), to give (I). each Ar = phenyl (optionally substituted by 1-5 R2 groups); R1 = 1-10C alkyl, aryl or arylalkyl (all optionally substituted); and R2 = halo, or 1-10C alkyl, aryl, arylalkyl, 1-10C alkoxy, acyloxy or amido (all optionally substituted). An Independent claim is included for enantiomerically pure compounds of formula (III) in which R1 is 1-10C alkyl or benzyl and Ar is unsubstituted phenyl.

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