Nitronate-aryne cycloaddition as a concise route to stereochemically complex fused benzisoxazolines and amino alcohols

Nitronate-aryne cycloaddition as a concise route to stereochemically complex fused benzisoxazolines and amino alcohols Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2023, Volume: 21, Number: 18, Pages: 3871-3880 Pages count : 10 DOI: 10.1039/d3ob00235g

Authors

Lukoyanov Alexander A. ¹ , Tabolin Andrey ¹ , Nelyubina Yulia V. ² , Aksenova Svetlana ^2,3 , Sukhorukov Alexey Yurievich ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Vavilov str. 28, Moscow, Russian Federation
3	Moscow Institute of Physics and Technology (National Research University), 141700, Institutskiy per. 9, Dolgoprudny, Moscow Region, Russian Federation

The reaction of cyclic nitronates (isoxazoline N-oxides and 5,6-dihydro-4H-1,2-oxazine N-oxides) with Kobayashi's aryne precursors affords tricyclic benzene-fused nitroso acetals as a result of [3 + 2]-cycloaddition. The process is regio- and stereoselective in most cases and produces the target cycloadducts possessing up to four contiguous stereogenic centers. These nitroso acetals were shown to be convenient precursors of valuable polysubstituted aminodiols through catalytic hydrogenolysis of the N–O bonds. Also, the action of protic acids resulted in an unusual fragmentation of the cyclic nitroso acetal moiety through heterolytic N–O bond cleavage and Beckmann-type reaction. Using this acid-mediated reaction, the synthesis of a hitherto unknown hexahydrobenzo[4,5]isoxazolo[2,3-a]azepine scaffold was accomplished.

Lukoyanov A.A. , Tabolin A. , Nelyubina Y.V. , Aksenova S. , Sukhorukov A.Y.
Nitronate-aryne cycloaddition as a concise route to stereochemically complex fused benzisoxazolines and amino alcohols
Organic & Biomolecular Chemistry. 2023. V.21. N18. P.3871-3880. DOI: 10.1039/d3ob00235g WOS Scopus OpenAlex

Web of science:	WOS:001004429800001
Scopus:	2-s2.0-85153965489
OpenAlex:	W4366537636

DB	Citing
OpenAlex	4
Scopus	5
Web of science	3