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Synthesis 2010(19): 3263-3267  
DOI: 10.1055/s-0030-1258210
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

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

Li Wanga, Zhi-Qian Wangb, Ming-Hua Xu*a,b, Guo-Qiang Lin*b
a Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China
b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
e-Mail: xumh@mail.shcnc.ac.cn; Fax: +86(21)50807388; e-Mail: lingq@mail.sioc.ac.cn;
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Publication History

Received 7 May 2010
Publication Date:
13 August 2010 (online)

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Abstract

A highly efficient asymmetric arylation of N-nosylimines with arylboronic acids catalyzed by a rhodium-diene complex is described. A wide range of enantiopure (98-99% ee) N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one, were obtained in high yields (83-99%) under very mild conditions.

Key words

asymmetric catalysis - amines - arylations - rhodium - diarylmethylamines

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