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Synfacts 2011(5): 0495-0495
DOI: 10.1055/s-0030-1259794
DOI: 10.1055/s-0030-1259794
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York(1,5)Naphthalenophanes via Photo-dehydro-Diels-Alder Cycloaddition
P. Wessig*, A. Matthes
Universität Potsdam, Germany
Further Information
Publication History
Publication Date:
15 April 2011 (online)
Significance
Ten naphthalenophanes 2 were prepared constructing the naphthalene core via photo-dehydro-Diels-Alder cycloaddition under mild conditions (λexc > 300 nm). The substrates (bis-ynones 1) are readily accessible in good yields via esterification, Sonogashira coupling, and oxidation, starting with the appropriate aryl iodides and 3-butyn-2-ol. The resulting naphthalenophanes are axially chiral and the enantiomers can be separated via chiral HPLC.