Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation
View Patent ↗The invention relates to a method for preparing a sulphoxide compound of formula (I) either as a single enantiomer or in an enantiomerically enriched form, comprising the steps of: a) contacting a pro-chiral sulphide of formula (II) with a metal chiral complex, a base and an oxidizing agent in an organic solvent; and optionally b) isolating the obtained sulphoxide of formula (I). wherein Ar, Y, R 1 are as defined in claim 1.
1. A compound selected from:
(−)2-[2-(4-chlorophenyl)benzyl]sulphinylacetamide;
(+)2-[2-(4-chlorophenyl)benzyl]sulphinylacetamide;
(−)2-[([1,1′-biphenyl]-2-ylmethyl)sulphinyl]acetamide; and
(+)2-[([1,1′-biphenyl]-2-ylmethyl)sulphinyl]acetamide;
wherein said compound has an enantiomeric excess of more than about 80%.
2. A compound according to claim 1 , wherein said compound is (−)2-[2-(4-chlorophenyl)benzyl]sulphinylacetamide.
3. A compound according to claim 1 , wherein said compound is (+)2-[2-(4-chlorophenyl)benzyl]sulphinylacetamide.
4. A compound according to claim 1 , wherein said compound is (−)2-[([1,1′-biphenyl]-2-ylmethyl)sulphinyl]acetamide.
5. A compound according to claim 1 , wherein said compound is (+)2-[([1,1′-biphenyl]-2-ylmethyl)sulphinyl]acetamide.
6. A compound according to claim 2 , wherein said compound has an enantiomeric excess of more than 90%.
7. A compound according to claim 2 , wherein said compound has an enantiomeric excess of more than 95%.
8. A compound according to claim 2 , wherein said compound has an enantiomeric excess of 99% or more.
9. A compound according to claim 3 , wherein said compound has an enantiomeric excess of more than 90%.
10. A compound according to claim 3 , wherein said compound has an enantiomeric excess of more than 95%.
11. A compound according to claim 3 , wherein said compound has an enantiomeric excess of 99% or more.
12. A compound according to claim 4 , wherein said compound has an enantiomeric excess of more than 90%.
13. A compound according to claim 4 , wherein said compound has an enantiomeric excess of more than 95%.
14. A compound according to claim 4 , wherein said compound has an enantiomeric excess of 99% or more.
15. A compound according to claim 5 , wherein said compound has an enantiomeric excess of more than 90%.
16. A compound according to claim 5 , wherein said compound has an enantiomeric excess of more than 95%.
17. A compound according to claim 5 , wherein said compound has an enantiomeric excess of 99% or more.