Imino-C-nucleoside Synthesis: Heteroaryl Lithium Carbanion Additions to a Carbohydrate Cyclic Imine and Nitrone

Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently to give a product from which further C-nucleoside analogues can be derived.