Beta-amino acids and methods and intermediates for making same

Abstract

Disclosed are β-amino acids that are unsubstituted in the β position; that are substituted in the β position with an aryl group; that are substituted in the α position with an aryl group; that bear two substituents in the α position; and/or that are substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring. Also disclosed are methods for making the above-mentioned β-amino acids and other β-amino acids which involve providing an α,β-unsaturated imide; converting the α,β-unsaturated imide to a 2-substituted-isoxazolidin-5-one; and converting the 2-substituted-isoxazolidin-5-one to a β-amino acid.

What is claimed is: 
     
         1 . A β-amino acid that is unsubstituted in the β position; that is substituted in the β position with an aryl group; that is substituted in the α position with an aryl group; that bears two substituents in the α position; and/or that is substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring. 
     
     
         2 . A β-amino acid according to  claim 1 , wherein said β-amino acid is unsubstituted in the β position. 
     
     
         3 . A β-amino acid according to  claim 1 , wherein said β-amino acid is substituted in the β position with an aryl group. 
     
     
         4 . A β-amino acid according to  claim 1 , wherein said β-amino acid is substituted in the α position with an aryl group. 
     
     
         5 . A β-amino acid according to  claim 1 , wherein said β-amino acid bears two substituents in the α position. 
     
     
         6 . A β-amino acid according to  claim 1 , wherein said β-amino acid is substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring. 
     
     
         7 . A method for making a β-amino acid comprising:
 converting a 2-substituted-isoxazolidin-5-one to a β-amino acid that is unsubstituted in the β position; that is substituted in the β position with an aryl group; that is substituted in the α position with an aryl group; that bears two substituents in the α position; and/or that is substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring. 
 
     
     
         8 . A method according to  claim 7 , wherein the β-amino acid is unsubstituted in the β position and wherein the 2-substituted-isoxazolidin-5-one is a 2-substituted-3-unsubstituted-isoxazolidin-5-one. 
     
     
         9 . A method according to  claim 7 , wherein the β-amino acid is substituted in the β position with an aryl group and wherein the 2-substituted-isoxazolidin-5-one is a 2-substituted-3-aryl-isoxazolidin-5-one. 
     
     
         10 . A method according to  claim 7 , wherein the β-amino acid is substituted in the α position with an aryl group and wherein the 2-substituted-isoxazolidin-5-one is a 2-substituted-4-aryl-isoxazolidin-5-one. 
     
     
         11 . A method according to  claim 7 , wherein the β-amino acid bears two substituents in the α position and wherein the 2-substituted-isoxazolidin-5-one is a 2-substituted-4,4-disubstituted-isoxazolidin-5-one. 
     
     
         12 . A method according to  claim 7 , wherein the β-amino acid is substituted in the α and β positions with groups which, together with the carbon atoms at the α and β positions, form a ring and wherein the 2-substituted-isoxazolidin-5-one is substituted in the 3 and 4 positions with groups which, together with the carbon atoms at the 3 and 4 positions, form a ring. 
     
     
         13 . A method according to  claim 7 , wherein said converting the 2-substituted-isoxazolidin-5-one to a β-amino acid is carried out using hydrogenation. 
     
     
         14 . A method for making a β-amino acid comprising:
 converting an α,β-unsaturated imide to a β-amino acid that is substituted in the α position, that is unsubstituted in the β position, and/or that bears an aryl substituent in the β position. 
 
     
     
         15 . A method according to  claim 14 , wherein the β-amino acid is substituted in the α position and wherein the α,β-unsaturated imide is an α-substituted-α,β-unsaturated imide. 
     
     
         16 . A method according to  claim 14 , wherein the β-amino acid is unsubstituted in the β position and wherein the α,β-unsaturated imide is a β-unsubstituted-α,β-unsaturated imide. 
     
     
         17 . A method according to  claim 14 , wherein the β-amino acid is substituted in the β position with an aryl group and wherein the α,β-unsaturated imide is a β-aryl-α,β-unsaturated imide. 
     
     
         18 . A method according to  claim 14 , wherein a hydrogen atom is bonded to the α-substituted-α,β-unsaturated imide's imide nitrogen. 
     
     
         19 . A method according to  claim 14 , wherein said converting the α-substituted-α,β-unsaturated imide to the α-substituted-β-amino acid is carried out using a chiral Lewis acid complex and hydrogenation. 
     
     
         20 . A 2-substituted-isoxazolidin-5-one that is unsubstituted in the 3 position; that is substituted in the 3 position with an aryl group; that is substituted in the 4 position with a non-methyl substituent; that is 4,4-disubstituted; and/or that is substituted in the 3 and 4 positions with groups which, together with the carbon atoms at the 3 and 4 positions, form a ring. 
     
     
         21 . An α,β-unsaturated imide that is substituted in the α position.