A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides. Issue 39 (26th September 2019)

• Record Type: Journal Article
• Authors: Teterina, Polina S.; Efremova, Mariia M.; Sirotkina, Ekaterina V.; Novikov, Alexander S.; Khoroshilova, Olesya V.; Molchanov, Alexander P.
• Is Part Of: Tetrahedron letters. Volume 60:Issue 39(2019)
• Publication Date: 2019-09-26
• Subjects: Nitrones -- Itaconimides -- Cycloaddition -- Reduction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151063
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: High efficient and selective synthesis of new 5-spiroisoxazolidines. High stereoselective 1, 3-dipolar cycloaddition of nitrones. New synthetic approach to spirolactones. Abstract: The 1, 3-dipolar cycloaddition of keto- and aldonitrones with N -arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts were subjected to reductive cleavage of the NO bond using zinc powder in acetic acid to give the corresponding spirolactones and 1, 3-amino alcohols.