Synthesis of (alkylaminomethyl)lactones and hydroxypiperidones using alkylaminomethylation methodology / Buev Evgeny M.,Moshkin Vladimir S.,Sosnovskikh Vyacheslav Y. // TETRAHEDRON LETTERS. - 2015. - V. 56, l. 47. - P. 6590-6592.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

We describe the reactions of carbonyl compounds bearing CO2R or CN groups with nonstabilized azomethine ylides. Oxazolidine-lactone rearrangement of the intermediate adducts was carried out for the first time to give (aminomethyl)lactones in good yields. The latter could be rearranged to give 5-hydroxy-2-piperidones, which could also be directly obtained from the aromatic ketones thus avoiding isolation of the intermediate lactone. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

Carbonyl compounds; Nonstabilized azomethine ylides; {[}3+2] Cycloaddition; 5-Aryloxazolidines; Lactones; 2-Piperidones NONSTABILIZED AZOMETHINE YLIDES; ALPHA-AMINO-ACIDS; ONE-POT SYNTHESIS; DECARBOXYLATIVE TRANSAMINATION; CYCLOADDITION REACTIONS; AROMATIC-ALDEHYDES; 5-ARYLOXAZOLIDINES; ROUTE; MECHANISM; DERIVATIVES

DOI:

10.1016/j.tetlet.2015.10.024

Web of Science ID:

ISI:000364885500014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 25
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	NONSTABILIZED AZOMETHINE YLIDES; ALPHA-AMINO-ACIDS; ONE-POT SYNTHESIS; DECARBOXYLATIVE TRANSAMINATION; CYCLOADDITION REACTIONS; AROMATIC-ALDEHYDES; 5-ARYLOXAZOLIDINES; ROUTE; MECHANISM; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	mvslc@mail.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	Russian Science Foundation {[}14-13-00388]
Funding-Text	This work was financially supported by the Russian Science Foundation (Grant 14-13-00388).
Number-of-Cited-References	38
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	11
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	CW3IL