Some diastereoselective enzyme-catalysed esterifications and interesterifications

Abstract

The alcohol bicycloheptenol (±)-1 or the corresponding acetate, (±)-5 couple with 2-(p-chlorophenoxy)propionic acid (±)-2 using lipases in organic solvents to give the ester bicycloheptenyl 2-(p-chlorophenyl)propionate (R,R)-3 with good/excellent selectivity. Similarly, 2-methoxycyclohexanol (±)-6 or the corresponding acetate (±)-7 undergo enzyme-induced coupling to the acid (±)-2 to form the (R,R,R)-ester 2-methoxycyclohexyl p-chlorophenoxyacetate 8 almost exclusively in a doubly enantioselective process.