Process for preparing cyclobutane-1,2-dicarboxylic esters

Details Process for preparing cyclobutane-1,2-dicarboxylic esters Process for preparing cyclobutane-1,2-dicarboxylic esters

1998-07-20

2000-02-15

Kight, John

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

549333, 549342, 549420, 549475, C07C 6974, C07D31906

Patent

active

060255196

ABSTRACT:
Cyclobutane-1,2-dicarboxylic esters of the formula: ##STR1## in which R.sup.1 is a C.sub.1-8 -alkyl group, an optionally substituted mono- or bicyclic cycloaliphatic group having 3 to 10 ring carbon atoms, an optionally substituted aryl or arylalkyl group or an optionally substituted saturated heterocyclic group and R.sup.2 is either C.sub.1-4 -alkyl or both radicals R.sup.2 together form a group of the formula --(CH.sub.2).sub.n --(n is 2 to 4), are prepared from the corresponding maleic or fumaric esters and ketene acetals in the presence of a Lewis acid and a sterically hindered base. The reaction is stereoselective when optically active maleic or fumaric esters are employed. The cyclobutane-1,2-dicarboxylic esters (I), in particular those having trans configuration, are intermediates in the synthesis of pharmaceutically active compounds.

REFERENCES:
patent: 5233076 (1993-08-01), Ahmad
patent: 5344962 (1994-09-01), Ahmad

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