LIC-KOR promoted nitrone reactivity: stereoselective synthesis of highly conjugated imines and secondary amines

• Published in: Tetrahedron letters Vol. 56; no. 42; pp. 5791 - 5794
• Main Authors: Parisotto, Stefano, Boggio, Paolo, Prandi, Cristina, Venturello, Paolo, Deagostino, Annamaria
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 14-10-2015
• Subjects: Alkoxydienes; Cyclopentenones; Imines; LIC-KOR superbase; Nitrones; LIC-KOR superbase; Nitrones; Cyclopentenones; Alkoxydienes; Imines
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.08.087

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•The reactivity of metalated alkoxy-1,3-dienes and α-aryl-N-phenylnitrones in the presence of LIC-KOR base has been studied.•A domino process permits the totally stereoselective synthesis of 2-ethoxy-N-phenyl-1-arylpenta-2,4-dien-1-imines.•The imines hydrolysis affords in good yields peptidomimetic functionalised 5-aryl-5-phenylaminocyclopentenones.
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.