SYNTHESIS AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF CHIRAL MALEIMIDES

New routes to the synthesis of various novel chiral maleimides are des cribed. The oxabicyclic anhydride 2 readily available exo-Diels-Alder adduct of furan and maleic anhydride was used as a vehicle, which in t urn reacted with hydrochlorides of amino acids 3a-f in the presence of Et3N with release of furan to give the requisite novel chiral imides 4a-f in good to moderate yields. The stereoselectivity of 1,3-dipolar cycloaddition of nitrile oxides with prepared chiral imides 4a-f is in vestigated.