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 contribution||Циклоприсоединение нитронов к 1,3-диарилпропенонам и последующие превращения образующихся изоксазолидинов|
|Number of pages||9|
|Journal||Chemistry of Heterocyclic Compounds|
|Early online date||19 Oct 2020|
|Publication status||Published - 19 Oct 2020|
Scopus subject areas
- Organic Chemistry