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Synthesis 2020; 52(20): 2987-3000
DOI: 10.1055/s-0040-1707897
DOI: 10.1055/s-0040-1707897
paper
Tetrasubstituted Furans by Nucleophile-Induced Cleavage of Carbonyl Ylide–DMAD Cycloadducts
Further Information
Publication History
Received: 06 May 2020
Accepted after revision: 27 May 2020
Publication Date:
20 July 2020 (online)
Abstract
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707897.
- Supporting Information
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