LIC‐KOR Promoted Nitrone Reactivity: Stereoselective Synthesis of Highly Conjugated Imines and Secondary Amines.

The reactivity of metalated alkoxy-1,3-dienes and α-aryl-N-phenylnitrones in the presence of LIC-KOR base, equimolar mixture of alkyllithium (LIC) and potassium alcoxides (KOR), (Schlosser, 1994) [1] has been studied. A cascade reaction involving a E1cb process stereoselectively affords ethoxy-N-phenyl-1-arylpenta-2,4-dien-1-imines. Their acidic hydrolysis allows the synthesis of peptidomimetic 5-aryl-5-phenylaminocyclopentenones in good yields.