Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1996-07-05
1999-10-05
Shippen, Michael L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
435135, 546135, 556418, 556427, 556438, 556445, 558432, 560 48, 560 76, 560 96, 560 64, 560231, 562503, C07C 6974
Patent
active
059627247
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a highly enantioselective process for the preparation of enantiomerically pure cyclopentane- and -pentene .beta.-amino acids.
The principle of an asymmetric ring opening of prochiral acid anhydrides with methanol and catalytic amounts of cinchona alkaloids is known from the publications J. Chem. Soc. Perkin Trans. I, 1987, 1053; Tetrahedron Asymm. 1990, 517 and J. Chem. Soc. Chem. Commun. 1985, 1717-1719. The corresponding half-esters are obtained with moderate enantiomeric excesses of from 35 to 67% of theory.
The invention relates to a highly enantioselective process for the preparation of enantiomerically pure cyclopentane- and -pentene .beta.-amino acids of the general formula (I). ##STR2## in which A and L denote hydrogen hydroxyl or represent straight-chain or branched alkyl having up to 8 carbon atoms which is optionally mono- to disubstituted by identical or different substituents consisting of halogen, hydroxyl, phenyl, benzyloxy or carboxyl or of straight-chain or branched alkoxy, acyl or alkoxycarbonyl having in each case up to 6 carbon atoms or of a group of the formula --NR.sup.4 R.sup.5, or straight-chain or branched alkyl having up to 6 carbon atoms, ##STR3## or .dbd.N--OH, in which halogen or straight-chain or branched alkyl, alkoxy or oxyacyl having in each case up to 8 carbon atoms, or denote benzyl or phenyl, branched alkyl having up to 8 carbon atoms which is optionally mono- to disubstituted by identical or different substituents consisting of hydroxyl or formyl or of straight-chain or branched acyl having up to 6 carbon atoms or of phenyl or benzoyl, which are optionally substituted up to 2 times by identical or different substituents consisting of halogen, nitro or cyano or of straight-chain or branched alkyl having up to 6 carbon atoms, or atoms or denotes benzyl or phenyl, the latter radicals being optionally substituted up to 3 times by identical or different substituents consisting of halogen, hydroxyl, nitro, cyano, trifluoromethyl or trifluoromethoxy or of straight-chain or branched alkyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or carboxyl or of the above-indicated group --NR.sup.4 R.sup.5, identical or different substituents consisting of halogen, hydroxyl, nitro, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkyl, acyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms or of a group of the formula --NR.sup.4 R.sup.5 or --SO.sub.2 R.sup.8, ##STR4## in which R.sup.9 denotes cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or hydrogen or denotes straight-chain or branched alkyl having up to 8 carbon atoms, mercapto or guanidyl or by a group of the formula --NR.sup.11 R.sup.12 or R.sup.13 --OC--, straight-chain or branched alkyl having up to 8 carbon atoms or phenyl, or denotes the above-indicated group --NR.sup.11 R.sup.12, atoms or by aryl having 6 to 10 carbon atoms which is substituted in turn by hydroxyl, halogen, nitro or alkoxy having up to 8 carbon atoms or by the group --NR.sup.11 R.sup.12, having up to 8 carbon atoms which is optionally substituted by phenyl, =CHR.sup.14, 8 carbon atoms which is optionally substituted by halogen, hydroxyl, phenyl or carboxyl or by straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, having up to 8 carbon atoms or phenyl, the latter radicals being optionally substituted up to 3 times by identical or different substituents consisting of hydroxyl, halogen, nitro, cyano, carboxyl, trifluoromethyl or trifluoromethoxy, of straight-chain or branched alkoxy, and in the case of phenyl also of straight-chain or branched alkyl, acyl or alkoxycarbonyl having in each case up to 6 carbon atoms, or of a group of the formula --NR.sup.4 R.sup.5 or --SO.sub.2 R.sup.8, formula (II) ##STR5## in which A, D, E and L have the meaning given above formula (III) having in each case up to 5 carbon atoms, which are optionally substituted by cyano, trimethylsilyl, phenyl or trichloromethyl, present in enantiom
REFERENCES:
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Arold Hermann
Fey Peter
Matzke Michael
Militzer Hans-Christian
Mittendorf Joachim
Bayer Aktiengesellschaft
Shippen Michael L.
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