Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene

Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene Full article

Journal

Journal of Organic Chemistry
ISSN: 0022-3263

Output data

Year: 2018, Volume: 83, Number: 10, Pages: 5392-5397 Pages count : 6 DOI: 10.1021/acs.joc.8b00085

Authors

Dobrynin Sergey A. ^1,2 , Glazachev Yuri I. ³ , Gatilov Yuri V. ¹ , Chernyak Elena I. ¹ , Salnikov George E. ^1,2 , Kirilyuk Igor A. ^1,2

Affiliations

1	(Данные Web of science) RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, SB, Academician Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Inst Chem Kinet & Combust, Inst Skaya 3, Novosibirsk 630090, Russia

A simple method for the synthesis of sterically shielded pyrrolidine nitroxides, including the title compound, has been suggested. The key procedure implies assembling the pyrrolidine ring from alpha-amino acid, ketone, and activated alkene in a three-component domino process, followed by oxidation to nitrone and Grignard reagent addition. The new nitroxides demonstrate very high stability against reduction with ascorbate.

Dobrynin S.A. , Glazachev Y.I. , Gatilov Y.V. , Chernyak E.I. , Salnikov G.E. , Kirilyuk I.A.
Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene
Journal of Organic Chemistry. 2018. V.83. N10. P.5392-5397. DOI: 10.1021/acs.joc.8b00085 WOS Scopus РИНЦ

Published online:	Apr 18, 2018
Published print:	May 18, 2018

Web of science	WOS:000432900800005
Scopus	2-s2.0-85046405890
Elibrary	35485846
OpenAlex	W2799809978