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CYCLOADDITION OF NITRONES TO 1,3-DIARYLPROPENONES AND SUBSEQUENT TRANSFORMATIONS OF THE RESULTING ISOXAZOLIDINES

Екатерина В. Сироткина, Мария М. Ефремова, Галина Л. Старова, Михаил А. Кузнецов, Александр П. Молчанов
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Abstract


Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1H,3H-furo[3,4-c]isoxazole-6a(6H)-carboxylates as single diastereomers.

Authors: Ekaterina V. Sirotkina, Mariia M. Efremova, Galina L. Starova, Mikhail A. Kuznetsov, Alexander P. Molchanov*


Keywords


chalcones; isoxazolidines; nitrones; 1,3-dipolar cycloaddition; reduction

Full Text: PDF (Russian) Supplementary File(s): Supporting information (2MB)


 

 

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