The First Asymmetric Intramolecular <i>Stetter</i> Reaction. Preliminary Communication
Helvetica Chimica ActaPublished 30 October 1996
Dieter Enders, Klaus Breuer, Jan Runsink, J. Henrique Teles
Citations297
SJR quartileQ2
SJR score0.49
SNIP0.45
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
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%.
Keywords
Chemistry
Journal of the American Chemical SocietyNuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters
2,573 Citations1973James A. Dale, Harry S. Mosher
Fortschritte der Chemie Organischer Naturstoffe/Fortschritte der Chemie organischer Naturstoffe/Progress in the chemistry of organic natural productsProgress in the Chemistry of Organic Natural Products 109
2,053 Citations2019A. Douglas Kinghorn, Heinz Falk +4 more
Angewandte Chemie International Edition in EnglishCatalyzed Addition of Aldehydes to Activated Double Bonds—A New Synthetic Approach
611 Citations1976Hermann Stetter
Helvetica Chimica ActaA Novel Asymmetric Benzoin Reaction Catalyzed by a Chiral Triazolium Salt. Preliminary communication
216 Citations1996Dieter Enders, Klaus Breuer +1 more
Angewandte ChemieDie katalysierte Addition von Aldehyden an aktivierte Doppelbindungen – Ein neues Syntheseprinzip
211 Citations1976Hermann Stetter
Helvetica Chimica ActaThe Chemistry of Stable Carbenes. Part 2. Benzoin‐type condensations of formaldehyde catalyzed by stable carbenes
185 Citations1996J. Henrique Teles, Johann‐Peter Melder +8 more
Tetrahedron LettersThe thiazolium catalyzed benzoin condensation with mild base does not involve a “dimer” intermediate
95 Citations1994Ronald Breslow, Ronald I. Kim
Angewandte Chemie International Edition in EnglishAsymmetric Nucleophilic Acylation via Metalated Chiral Amino Cyanides: Enantioselective Synthesis of 3‐Substituted 4‐Oxoesters by Asymmetric Michael Addition
43 Citations1990Dieter Enders, Peter Gerdes +1 more
Helvetica Chimica ActaEnantioselektive Synthese von Allyl‐, Propargyl‐ und 4‐En‐2‐inyl‐aminen durch 1,2‐Addition von Organocer‐Reagenzien an chirale Aldimine
40 Citations1995Dieter Enders, Jürgen Schankat
Tetrahedron AsymmetryDetermination of the absolute configuration of chiral secondary alcohols; new advances using 13C- and 2D-NMR spectroscopy
33 Citations1993Tõnis Pehk, É. Lippmaa +4 more
Angewandte ChemieAsymmetrische nucleophile Acylierung via metallierte chirale Aminocyanide; enantioselektive Synthese von 3‐substituierten 4‐Oxoestern durch asymmetrische Michael‐Addition
29 Citations1990Dieter Enders, Peter Gerdes +1 more
SynthesisAsymmetric Nucleophilic Acylation with Metalated Amino Nitriles: Diastereo- and Enantioselective Synthesis of 2-Substituted 3-Aroylcyclohexanones via Tandem Michael Addition/α-Alkylation
28 Citations1995Dieter Enders, Jochen Kirchhoff +2 more
Zeitschrift für Naturforschung AThe Structure of Lithiated Aminonitriles in Solution: Interpretation of their Experimental IR Spectra by Means of ab initio Calculations
23 Citations1991Gerhard Raabe, Elke Zobel +5 more
SynlettAsymmetric Nucleophilic Acylation with Metalated Chiral Amino Nitriles: Enantioselective Synthesis of 1,4-Diketones via Asymmetric Michael Addition
19 Citations2002Dieter Enders, Dietrich Mannes +1 more
Enzymemimetic C-C and C-N Bond Formations
18 Citations1994Dieter Enders
Synthesisβ-Lithiated Enamines as Enolate Equivalents in Michael Additions to Enoates. A Novel Entry to Mono- and Disubstituted 5-Oxo Esters
15 Citations1991Lucette Duhamel, Pierre Duhamel +5 more
Synlettβ-Lithiated Enamines as Enolate Equivalents in Asymmetric Michael Additions to Enoates. Highly Enantioselective Synthesis of Mono- and Disubstituted 5-Oxo Esters
14 Citations1992Dieter Enders, Wolfgang Karl