Diastereoselective Carboxyl Migrations of 3-Arylbenzofuranones

Mixed benzofuranyl carbonates derived from chiral chloroformates rearranged in the presence of nucleophilic catalysts to give C-carboxylated benzofurans with variable dr. The use of chiral nucleophilic catalysts gave modest improvement in dr, but better results were obtained by optimizing auxiliary...

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Veröffentlicht in:	Journal of organic chemistry 2008-02, Vol.73 (3), p.1158-1161
Hauptverfasser:	Peris, Gorka, Vedejs, Edwin
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzofurans - chemistry Carboxylic Acids - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Molecular Structure Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	Mixed benzofuranyl carbonates derived from chiral chloroformates rearranged in the presence of nucleophilic catalysts to give C-carboxylated benzofurans with variable dr. The use of chiral nucleophilic catalysts gave modest improvement in dr, but better results were obtained by optimizing auxiliary and catalyst. Thus, 8k was obtained with 9:1 dr.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo7021444