Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides

Abstract

New routes to the synthesis of various novel chiral maleimides are described. The oxabicyclic anhydride 2 readily available exo-Diels-Alder adduct of furan and maleic anhydride was used as a vehicle, which in turn 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 investigated.

Keywords

• Chiral maleimides
• 1
• 3-dipolar cycloadditions
• nitrile oxides
• stereoselectivity