Method for the preparation of optically active allylic esters

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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2604109N, 260463, 560 1, 560 84, 560 89, 560 90, 560 95, 560111, 560112, 560113, 560122, 560123, 560124, 560193, 560197, 560198, 560199, 560201, 560237, 560238, 560240, 560241, 560249, 560254, 560255, 560262, C07C 69145, C07C 6924, C07C 6978

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040693856

ABSTRACT:
In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.2 are each a hydrogen atom, or an alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, R.sub.3 is an alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, or when R.sub.3 is linked together with R.sub.2, they form a divalent hydrocarbon group including or not including a hetero atom and which is optionally substituted with a substituent having a hetero atom, and the asterisk (*) indicates an asymmetric carbon atom.

REFERENCES:
patent: 3956404 (1976-05-01), Walling
Kochi et al., J. Org. Chem., 30, 1862ff (1965).
Sosnovsky, Angew. Chem., Int. Ed. 3, 269-276 (1964).
Denny et al., J. Org. Chem., 30, 3151-3153 (1965).

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