Preparation of 2-amino-2′-hydroxy-1,1′-binaphthyl and N-arylated 2-amino-1,1′-binaphthyl derivatives via palladium-catalyzed amination

Palladium-catalyzed amination reactions were carried out with 2-triflato-2′-(4-methoxybenzyloxy)-1,1′-binaphthyl ( 5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2′-hydroxy-1,1′-binaphthyl ( 1). Arylamines were also c...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 6; pp. 1095 - 1098
Main Authors Singer, Robert A., Buchwald, Stephen L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.02.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Palladium-catalyzed amination reactions were carried out with 2-triflato-2′-(4-methoxybenzyloxy)-1,1′-binaphthyl ( 5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2′-hydroxy-1,1′-binaphthyl ( 1). Arylamines were also coupled successfully with 5 under similar conditions. Optically pure BINOL was converted to 1 in 61 % yield over several steps by using Pd-catalyzed amination methodology. In addition, N-arylated derivatives of 1 were prepared.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02642-2