Process for preparing chiral 3-triazolyl sulphoxide derivatives
View Patent ↗The present invention relates to a catalytic process for preparing 3-triazolyl sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form.
1. An enantiomerically enriched 3-triazolyl sulphoxide of formula (I),
wherein
X 1 and X 2 , Y 1 and Y 2 are each independently selected from the group consisting of fluorine, hydrogen, and (C 1 -C 6 )haloalkyl,
R 1 and R 2 are each independently selected from the group consisting of fluorine, and methyl, and
R 3 is amino,
where the enantiomer ratio is 60:40 to 99.5:0.5 (+):(−)enantiomer,
and wherein said 3-triazolyl sulphoxide of formula (I) is prepared by a process comprising reacting a sulphide of formula (II)
in which
each of X 1 , X 2 , Y 1 , Y 2 , R 1 , R 2 and R 3 is as defined above,
with an oxidizing agent, in a solvent, and in the presence of a chiral catalyst, at a reaction temperature between 10° C. and 60° C.,
wherein the oxidizing agent is hydrogen peroxide; and the chiral catalyst is a chiral metal-ligand complex comprising a transition metal and a chiral ligand, wherein the transition metal is vanadium, iron or manganese.
2. The 3-triazolyl sulphoxide of formula I according to claim 1 , wherein the enantiomer ratio is 75:25 to 90:10 (+):(−)enantiomer.
3. The 3-triazolyl sulphoxide of formula I according to claim 1 , wherein the enantiomer ratio is 60:40 to 95:5 (+):(−)enantiomer.
4. The 3-triazolyl sulphoxide of formula (I) according to claim 1 ,
in which
X 1 and X 2 , Y 1 and Y 2 are each independently selected from the group consisting of fluorine, and hydrogen.