Chiral catalysts and epoxidation reactions

A chiral catalyst having the following general formula:

• ##STR93## where M is a transition metal ion selected from the group consisting of Mn, Cr, Fe, Co, Ti, V. Ru, and Os;
• where A is an anion;
• where X1 and X3 are the same and are selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where X2, X4, Y1, Y2, Y3, Y4, Y5, and Y6 are independently selected from the group consisting of hydrogen, halides, alkyls, aryls, NO2, and alkyl groups bearing hetero atoms;
• where R1 and R4 are the same and are either selected from a first group consisting of H, CH.sub.3, C.sub.2 H.sub.5, and primary alkyls, or selected from a second group consisting of aryls, secondary alkyls, tertiary alkyls, and alkyls bearing hetero atoms;
• where R2 and R3 are the same and are either selected from said second group if R1 and R4 are selected from said first group, or selected from said first group if R1 and R4 are selected from said second group.

A chiral catalyst having the following general formula:

• ##STR94## where M is a transition metal ion in the +3 oxidation state;
• where 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 aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of X3 or X4 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of Y1 or Y2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, halides, NO.sub.2, and alkyl groups bearing hetero atoms;
• where at least one of Y4 or Y5 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, halides, NO.sub.2, and alkyl groups bearing hetero atoms;
• where Y3 and Y6 are independently selected from the group consisting of H and primary alkyl groups;
• where either one or two of R1, R2, R3 and R4 is hydrogen;
• where, if R1 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.

A chiral catalyst having the following general formula when in the active state:

• ##STR95## where M is a transition metal ion in the +3 oxidation state;
• where n is either 0, 1, or 2;
• where at least one of X1 or X2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of X3 or X4 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where Y1, Y2, Y3, Y4, Y5, and Y6 are independently selected from the group consisting of hydrogen, halides, alkyls, aryls, NO.sub.2, and alkyl groups bearing hetero atoms;
• where at least one of R1, R2, R3 and R4 is selected from a first group consisting of hydrogen, CH.sub.3, and primary alkyls;
• where, if R1 is selected from said first group, then R2 and R3 are selected from a second group consisting of aryls, secondary alkyls, tertiary alkyls, and alkyls bearing hetero atoms;
• where, if R2 is selected from said first group, then R1 and R4 are selected from said second group;
• where, if R3 is selected from said first group, then R1 and R4 are selected from said second group;
• and
• where, if R4 is selected from said first group, then R2 and R3 are selected from said second group.

A chiral catalyst having the following general formula when in the active state:

• ##STR96## where M is a transition metal ion selected from the group consisting of Mn, Cr, Fe, Co, Ti, V, Ru, and Os;
• where X1 and X3 are the same and are selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where X2, X4, Y1, Y2, Y3, Y4, Y5, and Y6 are independently selected from the group consisting of hydrogen, halides, alkyls, aryls, NO.sub.2, and alkyl groups bearing hetero atoms;
• where R1 and R4 are the same and are either selected from a first group consisting of H, CH.sub.3, C.sub.2 H.sub.5, and primary alkyls, or selected from a second group consisting of aryls, secondary alkyls, tertiary alkyls, and alkyls bearing hetero atoms;
• where R2 and R3 are the same and are either selected from said second group if R1 and R4 are selected from said first group, or selected from said first group if R1 and R4 are selected from said second group.

A chiral catalyst having the following general formula when in the active state:

• ##STR97## where M is a transition metal ion in the +3 oxidation state;
• where n is either 0, 1, or 2;
• where at least one of X1 or X2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of X3 or X4 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of Y1 or Y2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, halides, NO.sub.2, and alkyl groups bearing hetero atoms;
• where at least one of Y4 or Y5 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, halides, NO.sub.2, and alkyl groups bearing hetero atoms;
• where Y3 and Y6 are independently selected from the group consisting of H and primary alkyl groups;
• where either one or two of R1, R2, R3 and R4 is hydrogen;
• where, if R1 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.

A chiral catalyst having the following general formula:

• ##STR98## where n is either 0, 1, or 2;
• where at least one of X1 or X2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of X3 or X4 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where Y1, Y2, Y3, Y4, Y5, and Y6 are independently selected from the group consisting of hydrogen, halides, alkyls, aryls, NO.sub.2, and alkyl groups bearing hetero atoms;
• where at least one of R1, R2, R3 and R4 is selected from a first group consisting of hydrogen, CH.sub.3, and primary alkyls;
• where, if R1 is selected from said first group, then R2 and R3 are selected from a second group consisting of aryls, secondary alkyls, tertiary alkyls, and alkyls bearing hetero atoms;
• where, if R2 is selected from said first group, then R1 and R4 are selected from said second group;
• where, if R3 is selected from said first group, then R1 and R4 are selected from said second group;
• and
• where, if R4 is selected from said first group, then R2 and R3 are selected from said second group.

A chiral catalyst having the following general formula:

• ##STR99## where n is either 0, 1, or 2;
• where at least one of X1 or X2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of X3 or X4 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and alkyl groups bearing hetero atoms;
• where at least one of Y1 or Y2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, halides, NO.sub.2, and alkyl groups bearing hetero atoms;
• whereat least one of Y4 or Y5 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, halides, NO.sub.2, and alkyl groups bearing hetero atoms;
• where Y3 and Y6 are independently selected from the group consisting of H and primary alkyl groups;
• where either one or two of R1, R2, R3 and R4 is hydrogen;
• where, if R1 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.