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Enantioselective and Rapid Rh-Catalyzed Arylation of N-Tosyl- and N-Nosylaldimines in Methanol

Chun-Chih Chen, Balraj Gopula, Jin-Fong Syu, Jhih-Han Pan, Ting-Shen Kuo, Ping-Yu Wu, Julian P. Henschke and Hsyueh-Liang Wu*

*Department of Chemistry and Instrumentation Center, National Taiwan Normal University, No. 88, Section 4, Tingzhou Road Taipei 11677, Taiwan, Republic of China, Email: hlwntnu.edu.tw

C.-C. Chen, B. Gopula, J.-F. Syu, J.-H. Pan T.-S. Kuo, P.-Y. Wu, J. P. Henschke, H.-L. Wu, J. Org. Chem., 2014, 79, 8077-8085.

DOI: 10.1021/jo5012653



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Abstract

A catalyst prepared in situ from Rh(I) and a chiral diene ligand enables a rapid synthesis of enantiomerically enriched tosyl-protected diarylmethylamines from arylboronic acids and N-tosylaldimines under mild conditions. This addition offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt3 as a base.


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Key Words

diarylmethylamines


ID: J42-Y2014