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Synfacts 2006(8): 0806-0806  
DOI: 10.1055/s-2006-942010
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rh-Catalyzed Arylation of N-Tosylarylimines with Arylboronic Acids

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
H.-F. Duan, Y.-X. Jia, L.-X. Wang, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

The authors report a highly enantio­selective synthesis of diarylmethylamines. Many ligands were tested, and the use of a spiro mono­phosphite ligand (S)-ShiP was found to give the best results. In this report aryl boronic acids were shown to be good reagents for the addition to tosylimines. Rh(acac)(C2H4)2 emerged as the best catalyst precursor. Interestingly, KF as an additive was necessary to obtain the addition product in high yield. Imines with electron-donating and electron-withdrawing groups were tolerated. In addition, the deprotection was shown to proceed by treatment with SmI2 and HMPA in refluxing THF.