Compound reagents and method for synthesizing enantiomerically enriched amino acids
Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.
1. A compound or pharmaceutically acceptable salt thereof selected from the formula (I):
wherein
X is selected from O, S and NR 5 ;
R 1a and R 1b is optionally substituted aryl;
R 2 is hydrogen, optionally substituted alkyl;
R 3 is optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted aralkyl, optionally substituted heteroaralkyl, or optionally substituted heterocyclylalkyl;
R 4 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted heteroaralkyl, optionally substituted aralkyl or optionally substituted heterocyclylalkyl;
R 5 is hydrogen, alkyl, aryl, or arylalkyl.
2. The compound of claim 1 , wherein the compound of formula (I) is enantiomerically enriched for the R isoform.
3. The compound of claim 1 , wherein the compound is a compound of formula (Ia)
wherein the compound has an enantiomeric excess (ee) of at least about 50%.
4. The compound of claim 1 , wherein the compound is a compound of formula (Ib)
wherein the compound has an ee of at least about 50%.
5. The compound of claim 1 , wherein the compound of formula (I) is enantiomerically enriched for the S isoform.
6. The compound of claim 1 , wherein X is selected from O and S.
7. The compound of claim 6 , wherein X is S.
8. The compound of claim 1 , wherein R 1a is phenyl.
9. The compound of claim 1 , wherein R 1b is phenyl.
10. The compound of claim 1 , wherein the compound of formula (I) is selected from a compound of formula (Ic):
11. The compound of claim 1 , wherein the compound of formula (I) is selected from a compound of formula (Id):
wherein X 1 , X 2 , Y 1 and Y 2 are each independently selected from hydrogen, alkyl, alkoxy or haloalkyl.
12. The compound of claim 11 , wherein Y 1 or Y 2 is haloalkyl.
13. The compound of claim 1 , wherein the compound of formula (I) is