Diastereodivergency in the reactions of 3-metallated-2-methylbutanamide

Article abstract of DOI:10.1016/S0040-4020(97)10292-7

Diastereocontrolled reactions with 3-iodozinc-2-methylbutanamide were examined. When the iodozinc reagent was reacted with aromatic and α,β- unsaturated aldehydes in the presence of iodotrimethylsilane, C2-C3 anti- derivatives were obtained almost exclusively. Whereas, after transmetallation to Ti(IV), the reaction with aldehydes gave C2-C3 syn-derivatives exclusively. Acylation of the zinc reagent with acid chlorides in the presence of Pd(0) catalyst gave C2-C3 syn-derivatives.