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Synthesis 2011(16): 2671-2683  
DOI: 10.1055/s-0030-1260115
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Limno-CP: A Natural-Product-Inspired 5-Aryl-3(2H)-furanone as Scaffold for a Library of α-Modified Enones

Sabine Amslinger*, Simon K. Lindner
Universität Regensburg, Institut für Organische Chemie, Universitätstr. 31, 93053 Regensburg, Germany
Fax: +49(941)9434121; e-Mail: sabine.amslinger@chemie.uni-regensburg.de;
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Publikationsverlauf

Received 29 April 2011
Publikationsdatum:
14. Juli 2011 (online)

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Abstract

A library of 5-aryl-3(2H)-furanones that are modified in the α-position of the α,β-unsaturated carbonyl system was prepared via simple one- to three-step transformations from one common scaffold. The ¹³C NMR characterization of the enone system showed a strong influence of the α-substituents, especially on the shifts of the α- and β-carbon atoms. Probing the addition chemistry of nucleophiles versus our α-modified enones, a 1,2-addition-elimination­ was found, but no 1,4-addition.

Key words

furanones - substituent effects - enones - spiro compounds - 1,2-addition-elimination

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17

For the acid-induced cyclization of 4-hydroxy-1,3-diketones no spirocyclic compound is reported. Examples for monocyclic compounds are given in Ref. 1.