Synthesis of stereo-enriched bis glyco-cyclohexylamines by a one pot dual Petasis reaction.

[Display omitted] • First report on synthesis of stereoenriched bis glyco-cyclohexylamines via dual Petasis Reaction. • Plausible mechanism; OH directed anti -diastereoselection; N,N'-chelate organoboron complex assisted syn -diastereoselection. • Structures elucidated using HMBC, HSQC NMR experiments and X-ray single crystallographic analysis. • An efficient and simple catalyst free one pot synthesis using readily available inexpensive compounds was done. • All new compounds have been documented with good yields along with high de/ee. 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. [ABSTRACT FROM AUTHOR]