Stereoselective process

Details Stereoselective process Stereoselective process

1996-12-06

1998-01-13

Powers, Fiona T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548540, 549447, C07D295192, C07D31760, C07D40712

Patent

active

057081867

ABSTRACT:
This invention relates to a method for the stereoselective synthesis of a 2-aryloxycarboxylic acid using a chiral auxiliary to enhance the stereoselectivity of the alkylation of the .alpha.-halo acid with an aryloxy group.

REFERENCES:
patent: 4622415 (1986-11-01), Forster et al.
Durst et al., "Asymmetric Synthesis of alpha-Halo Esters", Tetra. Letters, vol. 33(45), 6799-6802, 1992.
Larsen, R.D., et al., "Alpha-Hydroxy Esters As Chiral Reagents: Asymmetric Synthesis of 2-Arylpropionic Acids", J. Am. Chem. Soc., vol. 111(19), pp. 7650-7653, 1989.
Koh, K., et al., "Stereoselective Sn2 Reactions Of The (R)-Pantolactone Ester Of Racemic Alpha-Halo Carboxylic Acids With Aryloxides. A Synthesis Of (S)-2-Aryloxy And (S)-2-Hydroxy Acids", J. Org. Chem., vol. 59(16), pp. 4683-4686, 1994.
Koh, K., et al., "A Facile Synthesis Of Optically Active C2-Symmetric 2,5-Disubistituted Pyrrolidines And Other Beta,Beta'-Dihydroxyamines", Tetra. Letters, vol. 35(3), pp. 375-378, 1994.
Koh, K., et al., "Reaction Of (R)-Pantolactone Esters Of Alpha-Bromoacids With Amines A Remarkable Synthesis Of Optically Active-Alpha-Amino Esters", Tetra. Letters, vol. 34(28), pp. 4473-4476, 1993.
Devine P.N., et al., "Stereoselective Synthesis Of 2-Aryloxy Acids From Lactamide Derived Esters Of Racemic Alpha-Halo Carboxylic Acids", Tetra. Letters, vol. 37(16), pp. 2683-2686, 1996.

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