The development of an approach toward sterically-hindered chiral 2′-aryl-1,1′-binaphthalenes functionalized at position 2 |
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Authors: | Michaela Me&scaron ková Martin Putala |
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Affiliation: | Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, SK-84215 Bratislava, Slovak Republic |
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Abstract: | Several approaches were examined for the preparation of 1,1′-binaphthalene derivatives bearing sterically demanding ortho-substituted aryl at position 2′ which are suitable for further functionalization at position 2. Steric hindrance of ortho-substituted aryl groups was critical for the approach through BINOL monotriflate. Among variations of cross-coupling reactions of 2,2′-dihalo-1,1′-binaphthalenes, Negishi arylation of an enantiopure 2,2′-dibromide was found to be the method of choice for regioselective and stereoconservative preparation of the target 2′-monoarylated precursor. Functionalization of the latter at position 2 was demonstrated by bromine substitution via lithiation followed by the reaction with several electrophiles. |
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Keywords: | Binaphthyl Negishi cross-coupling Palladium Phosphanylation Suzuki cross-coupling |
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