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Highly Enantioselective Synthesis of (Diarylmethyl)amines by Rhodium-Catalyzed Arylation of N-Nosylimines Using a Chiral Bicyclo[3.3.0]diene Ligand

Li Wang, Zhi-Qian Wang, Ming-Hua Xu*, Guo-Qiang Lin*

*Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China, Email: xumhmail.shcnc.ac.cn, lingqmail.sioc.ac.cn

L. Wang. Z.-Q. Wang, M.-H. Xu, G.-Q. Lin, Synthesis, 2010, 3263-3264.

DOI: 10.1055/s-0030-1258210



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Abstract

A highly efficient asymmetric arylation of N-nosylimines with arylboronic acids catalyzed by a rhodium-diene complex enables the synthesis of a wide range of enantiopure N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one in high yields under very mild conditions.

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Design of C2-Symmetric Tetrahydropentalenes as New Chiral Diene Ligands for Highly Enantioselective Rh-Catalyzed Arylation of N-Tosylarylimines with Arylboronic Acids

Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc., 2007, 129, 5336-5337.


Key Words

asymmetric catalysis, amines, arylations, rhodium, diarylmethylamines


ID: J66-Y2010-2680