Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy

Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2019, Volume: 361, Number: 23, Pages: 5322-5327 Pages count : 6 DOI: 10.1002/adsc.201901000

Authors

Ushakov Pavel Yu. ^1,2 , Khatuntseva Elizaveta A. ¹ , Nelyubina Yulia V. ³ , Tabolin Andrey A. ¹ , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ^4,1,5

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prospect, 47, Moscow, Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Leninskie gory, 1, str. 3, Moscow, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, 119991 Vavilov str. 28, Moscow, Russian Federation
4	D. Mendeleev University of Chemical Technology of Russia, 125047 Miusskaya sq., 9, Moscow, Russian Federation
5	Plekhanov Russian University of Economics, 117997 Stremyanny per. 36, Moscow, Russian Federation

A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N−O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated.

Ushakov P.Y. , Khatuntseva E.A. , Nelyubina Y.V. , Tabolin A.A. , Ioffe S.L. , Sukhorukov A.Y.
Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy
Advanced Synthesis & Catalysis. 2019. V.361. N23. P.5322-5327. DOI: 10.1002/adsc.201901000 WOS Scopus OpenAlex

Web of science:	WOS:000494115500001
Scopus:	2-s2.0-85074588372
OpenAlex:	W2979424969

DB	Citing
OpenAlex	22
Scopus	20
Web of science	21