Patent ID: 6031115
Filing Date: 2000-02-29
Classification: C07D

Abstract:
A process for preparing compounds of formula (B) ##STR15## wherein: one of A.sub.1 ' or A.sub.2 ' represents hydrogen and the other represents a group CF.sub.3 --Y-- wherein Y represents --CF.sub.2 --, >C.dbd.O, or --CH(OH)--, or A.sub.1 ' and A.sub.2 ' are groups convertible to A.sub.1 and A.sub.2 respectively;Y.sub.1 represents --O--, --CH.sub.2 -- or NR.sup.O wherein R.sup.O is hydrogen, alkyl or alkylcarbonyl; R.sub.1 and R.sub.2 independently represent hydrogen or alkyl; or R.sub.1 and R.sub.2 together represent a C.sub.2-7 polymethylene moiety;R.sub.3 represents hydrogen, hydroxy, alkoxy or acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together represent a bond;which process comprises reacting a compound of formula (C): ##STR16## wherein the variables A.sub.1 ', A.sub.2 ', Y.sub.1, R.sub.1 and R.sub.2 are as defined above, in the presence of an oxygen source and a chiral catalyst, wherein the chiral catalyst is selected from the group consisting of compounds with the structure of formula (D): ##STR17## wherein M is a transition metal ion, A is an anion, and n is either 0, 1, or 2; at least one of X1 or X2 is selected from the group consisting of silyl, aryl secondary alkyl and tertiary alkyl; and at least one of X3 or X4 is selected from the same group; Y1, Y2, Y3, Y4, Y5, and Y6 are independently selected from the group consisting of hydrogen, halide, alkyl, aryl group, silyl group, and alkyl group bearing hetero-atoms selected from the group consisting of alkoxy and halide; and at least one of R1, R2, R3 and R4 is selected from a first group consisting of H, CH.sub.3, C.sub.2 H.sub.5, and primary alkyl; wherein if R1is selected from said first group, then R2 and R3 are selected from a second group consisting of aryl groups, heteroatom-bearing aromatic groups, secondary alkyls and tertiary alkyls; if R2 is selected from said first group, then R1 and R4 are selected from said second groups if R3 is selected from said first group, then R1 and R4 are selected from said second group; if R4 is selected from said first group, then R2 and R3 are selected from said second group; orcompounds with the structure of formula (I): ##STR18## wherein M is a transition metal ion and A is an anion; where at least one of X1 or X2 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary alkyl, and hetero atoms; where at least one of X3 or X4 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary all, and hetero atoms; and where Y1, Y2, Y3, Y4, Y5, Y6, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, and Z12 are independently selected from the group consisting of hydrogen, halide, alkyl, aryl, and alkyl group bearing hetero atoms; orcompounds with the structure of formula (J): ##STR19## where M is a transition metal ion and A is an anion; where n is either 0, 1, or 2; where at least one of X1 or X2 is selected from the group consisting of aryl, primary alkyl, secondary alkyls tertiary alkyl, and hetero atoms, where at least one of X3 or X4 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary alkyl, and hetero atoms; where at least one of Y1 or Y2 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary alkyl, and hetero atoms; where at least one of Y4 or Y5 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary alkyl, and hetero atoms: where Y3 and Y6 are independently selected from the group consisting of hydrogen and primary alkyl groups; where either one or two of R1, R2, R3 and R4 is hydrogen; where, if R 1 is hydrogen, then R3 is a primary alkyl; where, if R2 is hydrogen, then R4 is a primary alkyl; where, if R3 is hydrogen, then R1 is a primary alkyl; and where, if R4 is hydrogen, then R2 is a primary alkyl; orcompounds with the structure of formula (K): ##STR20## where M is a transition metal ion and A is an anion; where n is either 3, 4, 5 or 6; where at least one of X1 or X2 is selected from the group consisting of aryl, primary alkyl, secondary alkyls tertiary alkyl, and hetero atoms, where at least one of X3 or X4 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary alkyl, and hetero atoms; where at least one of Y1 or Y2 is selected from the group consisting of aryl, primary alkyl, secondary alkyl, tertiary alkyls, and hetero atoms, where at least one of Y4 or Y5 is selected from the group consisting of aryl, primary alkyl secondary alkyl, tertiary alkyl, and hetero atoms: where Y3, and Y6 are independently selected from the group consisting of hydrogen and primary alkyl groups; where R1 and R4 are trans to each other and at least one of R1 and R4 is selected from the group consisting of primary alkyl and hydrogen; and where the carbons in the (C).sub.n portion have substituents selected from the group consisting of hydrogen, alkyl, aryl, and heteroatoms.