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Regio- and stereoselective (3 + 2)-cycloaddition reactions of nitrones with cyclic allenes. 2021
Mariia M Efremova, and
Anastasia A Makarova, and
Alexander S Novikov, and
Mariya A Kryukova, and
Mikhail A Kuznetsov, and
Alexander P Molchanov
Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, Saint Petersburg 199034, Russia. m.efremova@2012.spbu.ru.
An effective approach to access functionalized 2H-cyclonona(deca)[d]isoxazoles and 15-oxo-3,10-methanobenzo[b][1]azacyclododecines has been developed by the reaction of N-aryl-C,C-bis(methoxycarbonyl)nitrones with cyclonona(deca)-1,2-dienes in a one-pot fashion. The reaction of N-aryl-C-(phenylcarbamoyl)nitrones with these allenes proceeds strictly regioselectively giving the mixtures of diastereomeric isoxazolidines containing a double bond at the C4-position of the isoxazolidine ring. The quantum chemical calculations show that the regioselectivity of these reactions is in good agreement with the reactivity indices of the considered compounds.
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