Synthesis 2020; 52(20): 2987-3000
DOI: 10.1055/s-0040-1707897
paper
© Georg Thieme Verlag Stuttgart · New York

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

Matthias Dobesch
,
Julian Greiner
,
Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany   Email: gerhard.maas@uni-ulm.de
› Author Affiliations
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

 
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