Patent ID: 6350910
Filing Date: 2002-02-26
Classification: B01J,C07C,C07F

Abstract:
A process for stereospecific isomerisation of prochiral allyl systems represented by the formula in which R1â‰ R2 and each represents an alkyl or alkenyl group, containing 1 to 12 carbon atoms, or an aryl group, optionally substituted by a hydroxy group, R3 and R4 represent independently from one another hydrogen, a C1 to C12 alkyl or alkenyl group, or an aryl group, R5 is hydrogen or an alkyl or cycloalkyl group, containing 1 to 8 carbon atoms, R6 is an alkyl or cycloalkyl group, containing 1 to 8 carbon atoms, or R5 and R6 are taken together with nitrogen to form a ring having 6 atoms and containing oxygen, into enamines represented by the formula in which the symbols R1 to R6 have the meanings assigned above, or into imines represented by the formula in which the symbols R1 to R4 and R6 have the meanings assigned above and R5 is hydrogen, with the aid of catalysts of Rh, Ir or Ru having at least one chiral phosphine ligand, and in the presence of a solvent, the process being characterised in that the phosphine ligand is a ligand represented by the formula in which Ar represents a phenyl or tolyl group,R1 is a unit of the type Zâ€”Bâ€”, in which B is a group linking the polymer Z with the ligand, selected from among the groups â€”Oâ€”C(O)â€”(CH2)n, â€”NHâ€”C(O)â€”(CH2)nâ€”, Oâ€”(CH2)nâ€”, â€”NHâ€”(CH2)nâ€” and (CH2)nâ€”, n being a whole number from 1 to 10, and Z is a polymer or copolymer selected from among silica, polystyrene, polyamides, grafted copolymers having a low crosslinked polystyrene matrix on which polyethyleneglycol or polyoxyethylene is grafted, functionalised polystyrene of the Merrifield resin type, aminomethylated polystyrene, or (4-hydroxymethyl)phenoxymethyl) polystyrene; or in which the phosphine ligand is a ligand represented by formula â€ƒin which Ar is a phenyl or tolyl group, R2 and R3 represent hydrogen or a unit of the type Zâ€”Bâ€²â€”, Bâ€² being a group linking the polymer Z and the ligand, selected from among the groups â€”C(O)â€”, â€”(CH2)mâ€” or â€”NHâ€”C(O)â€”(CH2)mâ€”C(O)â€”, m being a whole number from 1 to 4, and Z being a polymer as defined above, R2&boxH;R3&boxH;H being excluded.