STEREOCHEMISTRY OF AMINOCARBONYL COMPOUNDS-X ; THE INFLUENCE OF THE AMINE MOIETY ON 1-2, 1-5 AND 1-6 ASYMMETRIC INDUCTION IN GRIGNARD ADDITIONS AND HYDRIDE REDUCTIONS

Article abstract of DOI:10.1016/S0040-4020(01)97970-0

The stereoselectivity of the title reactions due to a hindering amino group in α-asymmetric aminoketones (1 and 2) and to an asymmetric center far away from the reaction center in β-(methylpiperidino)-ketones (11-14) has been studied.The aminoalcohols obtained (3-8 and 15-22) have been separated in most cases and the relative configurations attributed by NMR.Based on diastereomeric ratios, a N-coordinated cyclic transition state has been proposed and is, effective for the Grignard reactions on the β-aminoketone system.