Kinetic Aldol Reactions of α-Keto Amides. Synthesis of the β-Methyl Glycosides of (-)-Cladinose and (+)-Mycarose

Article abstract of DOI:10.1021/jo00273a030

The first examples of nondehydrative, kinetic aldol condensations of 3-methyl and 3-phenoxy-2-oxo (tertiary) carboxamides are reported.Addition of hydride or methyl Grignard nucleophiles to the aldol products produced diol or monoprotected triol amides with high stereoselectivity in some cases.One of these compounds was elaborated to the methyl glycosides of (-)-cladinose and (+)-mycarose.