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Synthesis 2010(20): 3509-3519
DOI: 10.1055/s-0030-1258206
DOI: 10.1055/s-0030-1258206
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCopper(I)-Catalyzed Intramolecular Caryl-O Bond-Forming Cyclization for the Synthesis of 1,4-Benzodioxines and Its Application in the Total Synthesis of Sweetening Isovanillins
Weitere Informationen
Received
15 June 2010
Publikationsdatum:
13. August 2010 (online)
Publikationsverlauf
Publikationsdatum:
13. August 2010 (online)
Abstract
Various substituted 1,4-benzodioxines were synthesized through an Ullmann-type intramolecular Caryl-O coupling cyclization reaction using a catalytic amount of BINOL-CuI complex. This methodology was successfully utilized as the key step in the total synthesis of isovanillyl sweetening agents 5-(2,3-dihydro-1,4-benzodioxin-2-yl)-2-methoxyphenol and 5-(2,3-dihydro-1,4-benzoxathiin-2-yl)-2-methoxyphenol in 15.8% and 14.85% overall yields in five steps from isovanillin.
Key words
copper catalyst - 1,4-benzodioxines - BINOL ligand - Ullmann-type coupling - C-O bond formation
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- Supporting Information (PDF)
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