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The First Asymmetric Intramolecular <i>Stetter</i> Reaction. Preliminary Communication

Helvetica Chimica Acta · 1996 · Vol. 79(7) · pp. 1899–1902
Dieter EndersKlaus BreuerJan RunsinkJ. Henrique Teles

Abstract

Abstract The first asymmetric intramolecular Stetter reaction is reported, using the chiral triazolium salt 1 as catalyst. Starting from the easily accessible 4‐(2‐formylphenoxy)but‐2‐enoates 2 , this protocol opens up an enantioselective pathway to the benzo‐annulated pyran‐4‐ones (chroman‐4‐ones) 3a–h with good yields and enantiomeric excesses of up to 74%.

Synthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisChemistryEnantioselective synthesisIntramolecular forceEnantiomerCatalysisStereochemistryPyranSalt (chemistry)Organic chemistryCombinatorial chemistry
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N‐Heterocyclic Carbenes
Angewandte Chemie International Edition in English · 1997 · 1,675 citations
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