Asymmetric reaction of (RS)-2-phenylpropanal with chiral aluminium alkoxides. Part 1

Abstract

The reaction of chiral aluminium alkoxides (2)[(–)-menthyloxide (2a); (–)-2-methylbutoxide (2b); (–)-2-butoxide (2c); and (–)-2-bornanyl oxide (2d)] with (RS)-2-phenylpropanal (1) gives the optically active (S)-(–)-2-phenylpropyl (R)-(–)2-phenylpropanoate (3), and the mixed esters (–)-menthyl 2-phenylpropanoate (5a),(+)-2-phenylpropyl 2-methylbutanoate (4b), and (+)-2-methylbutyl 2-phenylpropanoate (5b), respectively. An asymmetric disproportionation reaction mechanism has been proposed for compound (1).