A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo{[}2,1-b]oxazoles / Moshkin Vladimir S.,Sosnovskikh Vyacheslav Ya. // MENDELEEV COMMUNICATIONS. - 2015. - V. 25, l. 6. - P. 440-442.

ISSN/EISSN:

0959-9436 / 1364-551X

Type:

Article

Abstract:

Diphenyloxapyrrolizidines, products of the reaction between proline and benzaldehyde, are convenient building blocks for synthesizing 2-substituted pyrrolidines. The opening of their oxazolidine ring by treatment with Grignard reagents has been performed and conditions for subsequent removal of the N-hydroxyethyl moiety have been found. Though the yields are moderate (36-42\%), the suggested synthesis of 2-alkyl(aryl)pyrrolidines is rather simple since it does not require purification of intermediate products and is easy scalable.

Author keywords:

ALPHA-SUBSTITUTED PYRROLINES; ONE-POT SYNTHESIS; AZOMETHINE YLIDE; ASYMMETRIC-SYNTHESIS; AROMATIC-ALDEHYDES; 3+2 CYCLOADDITIONS; TERTIARY-AMINES; CYCLIC IMINES; 5-ARYLOXAZOLIDINES; PYRROLIDINES

DOI:

10.1016/j.mencom.2015.11.014

Web of Science ID:

ISI:000367761800014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV-DEC
Publisher	ELSEVIER SCIENCE BV
Address	PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS
Language	English
EISSN	1364-551X
Keywords-Plus	ALPHA-SUBSTITUTED PYRROLINES; ONE-POT SYNTHESIS; AZOMETHINE YLIDE; ASYMMETRIC-SYNTHESIS; AROMATIC-ALDEHYDES; 3+2 CYCLOADDITIONS; TERTIARY-AMINES; CYCLIC IMINES; 5-ARYLOXAZOLIDINES; PYRROLIDINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	vladimir.moshkin@urfu.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	Russian Science Foundation {[}14-13-00388]
Funding-Text	This work was supported by the Russian Science Foundation (grant no. 14-13-00388).
Number-of-Cited-References	41
Usage-Count-Since-2013	1
Journal-ISO	Mendeleev Commun.
Doc-Delivery-Number	DA4HU