Doubly Vinylogous Aldol Reaction of Furoate Esters with Aldehydes and Ketones

Doubly Vinylogous Aldol Reaction of Furoate Esters with Aldehydes and Ketones

The use of bulky Lewis acids, aluminum tris­(2,6-diphenylphenoxide) (ATPH) and aluminum tris­(2,6-di-2-naphthylphenoxide) (ATNP), in the doubly vinylogous aldol reaction between methyl-5-methyl-2-furoate and aldehydes or ketones is described. These reactions proceed smoothly and in high yields with...

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Veröffentlicht in:Journal of organic chemistry 2017-01, Vol.82 (1), p.759-764
Hauptverfasser: Hartwig, William T, Sammakia, Tarek
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Esters - chemistry
Furans - chemistry
Ketones - chemistry
Molecular Structure
Vinyl Compounds - chemical synthesis
Vinyl Compounds - chemistry
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Zusammenfassung:The use of bulky Lewis acids, aluminum tris­(2,6-diphenylphenoxide) (ATPH) and aluminum tris­(2,6-di-2-naphthylphenoxide) (ATNP), in the doubly vinylogous aldol reaction between methyl-5-methyl-2-furoate and aldehydes or ketones is described. These reactions proceed smoothly and in high yields with both enolizable and non-enolizable substrates. This C–C bond-forming reaction enables a new bond construction for the synthesis of functionalized furans.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02473