Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds: a route to α-oxygenated oxime derivatives

Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds: a route to α-oxygenated oxime derivatives Full article

Journal

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

Output data

Year: 2019, Volume: 17, Number: 24, Pages: 5997-6006 Pages count : 10 DOI: 10.1039/c9ob01005j

Authors

Antonova Yulia A. ^1,2 , Nelyubina Yulia V. ³ , Sukhorukov Alexey Yu. ¹ , Ioffe Sema L. ¹ , Tabolin Andrey A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1, 119991 Moscow, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russian Federation

A new tandem double acylation/rearrangement reaction of nitro compounds is described. It has a broad substrate scope allowing the mild and efficient synthesis of α-acyloxy oxime esters in high yields and regioselectivity. According to the obtained data, the mechanism for transformation was proposed. The utility of the obtained α-hydroxy oxime esters was demonstrated.

Antonova Y.A. , Nelyubina Y.V. , Sukhorukov A.Y. , Ioffe S.L. , Tabolin A.A.
Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds: a route to α-oxygenated oxime derivatives
Organic & Biomolecular Chemistry. 2019. V.17. N24. P.5997-6006. DOI: 10.1039/c9ob01005j WOS Scopus OpenAlex

Web of science:	WOS:000471907500018
Scopus:	2-s2.0-85067480170
OpenAlex:	W2947601076

DB	Citing
OpenAlex	8
Scopus	8
Web of science	6