Preparation of chiral 1,2-diols, useful as intermediates e.g. for pharmaceuticals, agrochemicals, cosmetics and chiral polymers, by hydroxylation of an olefin in the presence of oxygen, an osmium compound and a chiral amine

摘要

Preparation of mono-, bi and/or polyfunctional chiral 1,2-diols (I), by osmium-catalyzed asymmetric dihydroxylation of olefins, involves reacting an olefin (II) with molecular oxygen in presence of an osmium compound and a chiral amine ligand (III) in water (or a water-containing solvent) at pH 8.5-13. Preparation of chiral 1,2-diols of formula (I) involves reacting an olefin of formula (II) with molecular oxygen in the presence of an osmium compound catalyst and a chiral amine ligand (III) in water (or a water-containing solvent) at pH 8.5-13. R1-R4 = H, A, CN, COOH, COOA, COOAr, COA, COAr, OA, OAr, OCOAr, OCOA, OCOOA, N(A)2, NHA, N(Ar)2, NO, NO2, NOH, Ar, halo, Si(A)3, CHO, SO3H, SO3A, SO2A, SOA, CF3, NHCOA, CONH2, CONHA, NHCHO, NHCOOA, CHCHCOO, CHCHCOOH, P(O)(Ar)2, P(O)(A)2, PO3H2 or P(O)(OA)2; A = linear, branched and/or cyclic hydrocarbyl (optionally substituted by 1-6 Q); Ar = 5-7 membered, optionally fused aromatic ring containing 4-14C and 0-3 heteroatoms (e.g. N, O or S), optionally substituted by 1-6 Q; Q = A, OA, OCOA, OAr, Ar, halo, OH, NO2, NO, Si(A)3, CN, COOH, CHO, SO3H, NH2, NHA, N(A)2, P(O)(A)2, SO2A. SOA, CF3, NHCOA, COOA, CONH2, COA, NHCHO, NHCOOA, COAr, COOAr, P(O)(Ar)2, PO3H2, P(O)(OA)2 or SO3A.