Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral α,α-disubstituted 1,3-propanediols

Article abstract of DOI:10.1016/S0957-4166(96)00500-9

The asymmetric differentiation by lipase-catalysed transesterification of prochiral α,α-disubstituted 1,3-propanediols 5 and 11 was accomplished in good enantiomeric excess and high chemical yield. The absolute configuration of the corresponding monoacetates (+)-2a and (-)-12a were determined by conversion into known key intermediates used in the synthesis of (-)-aphanorphine and (+)-eptazocine.