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.

Translated title of the contributionЦиклоприсоединение нитронов к 1,3-диарилпропенонам и последующие превращения образующихся изоксазолидинов
Original languageEnglish
Pages (from-to)1193-1201
Number of pages9
JournalChemistry of Heterocyclic Compounds
Volume56
Issue number11
Early online date19 Oct 2020
DOIs
Publication statusPublished - 19 Oct 2020

Scopus subject areas

  • Organic Chemistry

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