AU2001230179A1 - Method for the enantioselective preparation of 3,3-diphenyl-2,3-epoxy propionic acid esters - Google Patents

Method for the enantioselective preparation of 3,3-diphenyl-2,3-epoxy propionic acid esters

Info

Publication number
AU2001230179A1
AU2001230179A1 AU2001230179A AU3017901A AU2001230179A1 AU 2001230179 A1 AU2001230179 A1 AU 2001230179A1 AU 2001230179 A AU2001230179 A AU 2001230179A AU 3017901 A AU3017901 A AU 3017901A AU 2001230179 A1 AU2001230179 A1 AU 2001230179A1
Authority
AU
Australia
Prior art keywords
diphenyl
ester
acid esters
propionic acid
enantioselective preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
AU2001230179A
Inventor
Rolf Jansen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of AU2001230179A1 publication Critical patent/AU2001230179A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Abstract

The invention relates to a process for the enantioselective preparation of glycide ester (I) by(a) dihydroxylation of a corresponding 3-phenyl cinnamate (II) by osmium (VIII) oxide catalysis in the presence of a Sharpless ligand and an oxidizing agent to form the dihydroxy ester (III),(b) selective conversion of the hydroxy function in position 2 of the dihydroxy ester (III) to a leaving group,(c) intramolecular substitution of the leaving group through the hydroxy function in position 3 to form the glycide ester (I),in whichR1 denotes C1-C10 alkyl, aryl, or arylalkyl, which may be substituted,R2 denotes C1-C10 alkyl, aryl, arylalkyl, halogen, C1-C10 alkoxy, acyloxy, or amide, which may be substituted, andn is 0 to 5.
AU2001230179A 2000-01-20 2001-01-12 Method for the enantioselective preparation of 3,3-diphenyl-2,3-epoxy propionic acid esters Abandoned AU2001230179A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10002393A DE10002393A1 (en) 2000-01-20 2000-01-20 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
DE10002393 2000-01-20
PCT/EP2001/000322 WO2001053281A1 (en) 2000-01-20 2001-01-12 Method for the enantioselective preparation of 3,3-diphenyl-2,3-epoxy propionic acid esters

Publications (1)

Publication Number Publication Date
AU2001230179A1 true AU2001230179A1 (en) 2001-07-31

Family

ID=7628194

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2001230179A Abandoned AU2001230179A1 (en) 2000-01-20 2001-01-12 Method for the enantioselective preparation of 3,3-diphenyl-2,3-epoxy propionic acid esters

Country Status (10)

Country Link
US (1) US6677465B2 (en)
EP (1) EP1248775B1 (en)
JP (1) JP3817478B2 (en)
AT (1) ATE261950T1 (en)
AU (1) AU2001230179A1 (en)
CA (1) CA2397585A1 (en)
DE (2) DE10002393A1 (en)
ES (1) ES2218374T3 (en)
MX (1) MXPA02007077A (en)
WO (1) WO2001053281A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19533023B4 (en) 1994-10-14 2007-05-16 Basf Ag New carboxylic acid derivatives, their preparation and use
CN103709106A (en) * 2013-12-06 2014-04-09 石家庄博策生物科技有限公司 Stereoselectivity preparation method for Letairis

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19533023B4 (en) 1994-10-14 2007-05-16 Basf Ag New carboxylic acid derivatives, their preparation and use

Also Published As

Publication number Publication date
DE50101704D1 (en) 2004-04-22
EP1248775B1 (en) 2004-03-17
DE10002393A1 (en) 2001-07-26
ES2218374T3 (en) 2004-11-16
WO2001053281A1 (en) 2001-07-26
CA2397585A1 (en) 2001-07-26
JP2003527354A (en) 2003-09-16
US6677465B2 (en) 2004-01-13
ATE261950T1 (en) 2004-04-15
US20030162982A1 (en) 2003-08-28
EP1248775A1 (en) 2002-10-16
MXPA02007077A (en) 2003-03-27
JP3817478B2 (en) 2006-09-06

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