Stereocontrolled addition of chiral, non-racemic amide homoenolates to t-Boc-(S)-phenylalaninal

Article abstract of DOI:10.1016/S0040-4039(00)60995-4

The reaction of chiral indanolamide homoenolates 4a and 4c with t-Boc-(S)-phenylalaninal 3 exclusively gave the non-chelation product in contrast to the propionate ester homoenolate 7c, ^1a which gives predominantly the chelation controlled product. However, the reaction of simple achiral amide homoenolates 7a and 7b with 3 was nonselective.