Synfacts 2011(3): 0290-0290  
DOI: 10.1055/s-0030-1259480
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Addition of Arylboronic Acids to 3-Indolylimines

Contributor(s): Mark Lautens, Jane Panteleev
H.-Y. Yang, M.-H. Xu*
Shanghai Institute of Materia Medica, P. R. of China
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Publikationsverlauf

Publikationsdatum:
16. Februar 2011 (online)

Significance

The authors report on the addition of arylboronic acids to tosyl-protected indolyl­imines. The enantioselective reaction of arylbo­ronic acids with imines under rhodium catalysis is well documented (see, for example: M. Kuriyama, T. Soeta, X. Hao, Q. Chen, K. Tomioka J. Am. Chem. Soc. 2004, 126, 8128; H. Nakagawa, J. C. Rech, R. W. Sindelar, J. A. Ellman Org. Lett. 2007, 9, 5155). The authors utilize their bicyclo-[3,3,0]diene ligand, which was earlier shown to be efficient in similar reactions (J. Am. Chem. Soc. 2007, 129, 5336). This protocol gives an alternative access point to 3-indolyl-methanamines, which are otherwise obtained using enantioselective Friedel-Crafts chemistry.