Abstract
A one pot dual Petasis reaction of sugars, styrene boronic acid and cis/trans 1,2-cyclohexyldiamines was done for the diastereoselective synthesis of bis glyco-cyclohexylamines, which have multiple stereogenic centres and coordinating heteroatoms. The products were isolated and characterized by HMBC, HSQC, 1H, 13C NMR experiments, and X-ray single crystallographic analysis. A plausible mechanism for the dual Petasis reaction was proposed that involves hydroxyl directed borylation for the anti-diastereoselectivity along with N,N'-chelate tetracoordinated organoboron complex assisted syn-diastereoselectivity based on the experimental findings.
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