Synthesis of novel D-glucose based anionic bolaamphiphiles and their catalytic application in 1,3-dipolar nitrone cycloaddition reactions

Three D-glucose based bolaamphiphiles have been synthesized by a simple and efficient synthetic methodology utilizing the free C-3 hydroxyl group of diisopropylidene glucose. The resulting bolaamphiphiles showed unique aggregation behavior in aqueous solution, e.g. transformation of vesicle to tubular morphology on aging. The chiral hydrophobic interior of these vesicles was utilized as tiny reaction vessels to carry out 1,3-dipolar nitrone cycloadditions in water. The corresponding isoxazolidine derivatives were formed with high diastereoselectivity in several cases. The bolaamphiphile with 12 carbon spacer (5c) showed better diastereoselectivity among the rest with just 2 mol% of catalyst loading and can be reused. (C) 2017 Elsevier B.V. All rights reserved.