Organometallic Additions to β-substituted N-Boc-β-aminoaldehydes: a New Synthesis of Enantiomerically Pure 1,3-disubstituted N-Boc-1,3-aminoalcohols

1,2-addition of organolithium and organomagnesium derivatives to β-substituted (N-Boc)-β-aminoaldehydes gave access to enantiomerically pure, 1,3-disubstituted, 1,3-aminoalcohols. A diastereoselective version of this addition was also investigated and Gilman cuprates were found to add onto aldehydes 1a–b with notable diastereoselectivity (up to 70% de) in favour of the anti isomer. The absolute configuration of each obtained 1,3-aminoalcohol was determined.