Tetrasubstituted Furans by Nucleophile-Induced Cleavage of Carbonyl Ylide–DMAD Cycloadducts

Autor:	Julian Greiner, Gerhard Maas, Matthias Dobesch
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Tandem 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry 010402 general chemistry Cleavage (embryo) 01 natural sciences Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound Nucleophile Ylide Furan Moiety Carbenoid
Zdroj:	Synthesis.
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0040-1707897
Popis:	Compounds incorporating a 4-aza-8-oxabicyclo[3.2.1]oct-6-en-2-one moiety, which were prepared by a tandem carbenoid carbonyl ylide cyclization/[3+2]-cycloaddition reaction from ethyl 2-diazo-3-oxo-4-phthalimidobutanoates, undergo a nucleophile-induced two-bond ring cleavage when treated with protic heteronucleophiles. In this manner, tetrasubstituted furantricarboxylates, tethered with α-amino acids, esters, thioesters, and amides by a 2-carbonylphenyl moiety, are obtained.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::67231de6cf45782ba70eb9130ab184a0 https://doi.org/10.1055/s-0040-1707897 Zobrazit plný text záznamu