Abstract
We disclose an efficient molecular I2/[bmim]OH-catalyzed activation of carbohydrates as aldehyde equivalent for synthesis of imino/-thiosugar annulated β-lactams in excellent yield (86–94%) and high cis diastereoselectivity (96–99%). The envisaged method involves reaction of unprotected d-glucose/d-xylose as 1C, masked amino/-mercapto acid as 2C, and aromatic amines as N source in the present three-component synthesis. The reaction is effected via intramolecular aza-Michael addition followed by amino/-mercaptoacetylative cyclization in a one-pot procedure. The developed methodology for β-lactam synthesis has advantage of its operational simplicity, ambient reaction conditions, and the ionic liquid, [bmim]OH could be easily recycled for further use without any loss of efficiency.
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