STUDIES ON THE REACTION OF α-IMINO ESTERS WITH ORGANOMETALLIC COMPOUNDS

Article abstract of DOI:10.1016/S0040-4020(01)86047-6

Benzylzinc reagent reacted with α-amino ester ( 2 ) at the α-carbon exclusively, though other organometallic reagents such as Mg, Al, Cu, Ti, and B derivatives reacted at the nitrogen atom.Use of the (S)-amine as a chiral auxiliary of 2 created the R chirality at the imino carbon.Very high chiral induction was realized in the reaction of prenylzinc reagent with α-imino 8-(-)phenylmenthyl ester ( 10 ).The reaction of 2 with heteroatom substituted allylic organometallic compounds ( 15 ) gave the corresponding α-heteroatom substituted amino acid derivatives ( 16 ).Here again, the allylic zinc reagent gave the adduct in higher yield than the corresponding Ti, Al, and B reagents.