Process for preparing chiral compounds
AssigneeUniversity Court of the University of St Andrews
InventorDavid O'Hagan
Life of this patent
Estimating the term…
Abstract
Process for the preparation of chiral compounds of formula (I) comprising contacting a compound of formula (II) with a source of hydrogen or halide; wherein A is a chiral center; X is selected from oxygen, sulphur and nitrogen; n is selected from 0 and 1 and is equal to the valence of X less 2; B is a fragment CR 3 2; Z is hydrogen or halogen; with the proviso that when X is nitrogen, n is 1, one of R 1 and two of R 2 are hydrogen, BZ is CHPh 2, the other R 1 and R 2 do not form together a five membered heterocyclic (pyrrolidone) ring; novel intermediates, novel compounds, polymers and libraries thereof and the use thereof as fine chemicals, and compositions thereof.
Claims9
An enantiomerically pure compound of the formula I wherein X is N and n is 1
- wherein
- A is an enantiomerically pure centre CH;
- Z is hydrogen or fluoro;
- and wherein
- R1 is selected from hydrogen or from straight chain or branched, saturated or unsaturated C1-8 hydrocarbon optionally substituted by one or more hydroxy, halo, aryl, cyclo C1-8 alkyl;
- each R3 is independently selected from halo, except when Z=F, then R3≠F;
- or straight or branched chain, saturated or unsaturated C1-4 alkyl, alkenyl, alkynyl or aryl;
- each optionally substituted by hydroxy, halo, saturated or unsaturated C1-4 alkyl, alkenyl or alkynyl, aryl, cyclo C1-6 alkyl, carbonyl, carboxyl, amino, amido;
- each R2 is independently selected from hydrogen, straight chain or branched, saturated or unsaturated C1-8 alkyl, alkenyl, or alkynyl;
- each optionally substituted by hydroxy, aryl, cyclo C1-6 alkyl, carbonyl, carboxyl, amino, amido, or aryl;
- and
- one R1 and one of R2 together may form an alkylene group as part of a heterocyclic ring;
- with the proviso that when two of R2 are hydrogen, CR32 is CPh2 and Z is hydrogen, R1 and the other R2 do not form together a five membered heterocyclic (pyrrolidone) ring;
- and wherein CR32Z does not comprise a chiral center.
Dependencies are inferred from the claim text.