Diastereoselective reactions of Grignard reagents with chiral amino lactols derived from L-aspartic acid

Article abstract of DOI:10.1016/S0957-4166(00)86164-9

Nucleophilic additions to chiral amino lactols obtained from L-aspartic acid containing a chiral α-silyloxymethyl function by simple Grignard reagents exhibited high stereoselectivity to provide the corresponding optically active amino alcohols containing three contiguous stereogenic centers. The mechanistic origin of the asymmetric induction is rationalized based on chelation controlled models.