Process for epoxidising prochiral olefins and a catalyst therefo

Details Process for epoxidising prochiral olefins and a catalyst therefo Process for epoxidising prochiral olefins and a catalyst therefo

1996-08-05

1999-06-29

Lipman, Bernard

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

5253328, 5253329, 5253331, 5253332, 552524, 552525, 552531, 552533, C08F 808

Patent

active

059169753

DESCRIPTION:

BRIEF SUMMARY
This invention relates to a novel process for preparing epoxides from olefins and in particular chirally enriched epoxides, certain novel catalysts used in such process and compounds associated with the process.
WO 91/14694 describes certain catalysts of the following formula (I): ##STR1## in which
M is a transition metal ion, A is an anion, and n is either 0, 1 or 2. At least one of X.sub.1 or X.sub.2 is selected from the group consisting of silyls, aryls, secondary alkyls and tertiary alkyls; and at least one of X.sub.3 or X.sub.4 is selected from the same group. Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, Y.sub.5 and Y.sub.6 are independently selected from the group consisting of hydrogen, halides, alkyls, aryl groups, silyl groups, and alkyl groups bearing heteroatoms such as alkoxy and halide. Also, at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is selected from a first group consisting of H, CH.sub.3, C.sub.2 H.sub.5 and primary alkyls. Furthermore, if R.sub.1 is selected from said first group, then R.sub.2 and R.sub.3 are selected from a second group consisting of aryl groups, heteroatom-bearing aromatic groups, secondary alkyls and tertiary alkyls. If R.sub.2 is selected from said first group, then R.sub.1 and R.sub.4 are selected from said second group. If R.sub.3 is selected from said first group, then R.sub.1 and R.sub.4 are selected from said second group. If R.sub.4 is selected from said first group, then R.sub.2 and R.sub.3 are selected from said second group. Such catalysts are described as being useful in enantioselectively epoxidising a prochiral olefin.
In addition WO 91/14694 describes certain catalysts of the formula shown below, herein referred to as formula (IA): ##STR2## where M is defined as a transition metal ion and A is an anion; where n is either 3,4,5 or 6; where at least one of X.sub.1 or X.sub.2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and hetero atoms; where at least one of X.sub.3 or X.sub.4 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and hetero atoms; where at least one of Y.sub.1 or Y.sub.2 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and hetero atoms; where at least one of Y.sub.4 or Y.sub.5 is selected from the group consisting of aryls, primary alkyls, secondary alkyls, tertiary alkyls, and hetero atoms; where Y.sub.3, and Y.sub.6 are independently selected from the group consisting of hydrogen and primary alkyl groups; where R.sub.1 and R.sub.4 are trans to each other and at least one of R.sub.1 and R.sub.4 is selected from the group consisting of primary alkyls and hydrogen; and where the carbons in the (C)n portion have substituents selected from the group consisting of hydrogen, alkyl, aryl, and heteroatoms.
Such catalysts are described as being useful in enantioselectively epoxidising a prochiral olefin. These catalysts belong to the class of catalysts known in the art as `salen catalysts`.
Co-pending International Patent Application Number PCT/GB93/01666 (now International Patent Application, Publication Number WO 94/03271) also discloses a series of salen catalysts, structurally distinct from the catalysts of formula (I) and having the general formula (II): ##STR3## in which M is a transition metal ion;
A is a counter-ion if required;
r, s and t are independently 0 to 3 such that r+s+t is in the range of 1 to 3;
R.sup.a, R.sup.b, R.sup.c are each independently hydrogen or CH.sub.2 OR' where R' is hydrogen or an organic group;
B and E are independently oxygen, CH.sub.2, NR.sup.d in which R.sup.d is alkyl, hydrogen, alkylcarbonyl, or arylcarbonyl or SO.sub.n where n is 0 or an integer 1 or 2, with the proviso that B and E are not simultaneously CH.sub.2 and that when B is oxygen, NR.sup.d or SO.sub.n, then r cannot be 0, and when E is oxygen, NR.sup.d or SO.sub.n, then t cannot be 0;
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are independently hydrogen

REFERENCES:
patent: 3787501 (1974-01-01), Kallianos et al.
patent: 4861904 (1989-08-01), Sugie et al.
patent: 5266565 (1993-11-01), Lacoste et al.
patent: 5281578 (1994-01-01), Bradley et al.
J. Org. Chem, 56, pp. 2296-2298 (1991).

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