α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

Autor:	Mikhail S. Novikov, Dmitry Dar'in, Judith Synofzik, Mikhail Krasavin, Olga Bakulina, Grigory Kantin
Rok vydání:	2019
Předmět:	chemistry.chemical_compound Transition metal 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Lactam Staudinger synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis
Zdroj:	The Journal of Organic Chemistry. 84:12101-12110
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b02030
Popis:	Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::af3a199b726b0a498ae0e47b99d760e1 https://doi.org/10.1021/acs.joc.9b02030 Zobrazit plný text záznamu