Method for the enantioselective preparation of 3,3-diphenyl-2,3-epoxy propionic acid esters
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United States of America Patent
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Jan 13, 2004
Grant Date -
Aug 28, 2003
app pub date -
Oct 29, 2002
filing date -
Jan 20, 2000
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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), ##STR1## in which R.sub.1 denotes C.sub.1 -C.sub.10 alkyl, aryl, or arylalkyl, which may be substituted, R.sub.2 denotes C.sub.1 -C.sub.10 alkyl, aryl, arylalkyl, halogen, C.sub.1 -C.sub.10 alkoxy, acyloxy, or amide, which may be substituted, and n is 0 to 5.
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