Highly Enantioselective Rh-Catalyzed Alkenylation of Imines: Synthesis of Chiral Allylic Amines via Asymmetric Addition of Potassium Alkenyltrifluoroborates to N-Tosyl Imines
Balraj Gopula, Chien-Wei Chiang, Way-Zen Lee, 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: hlw
ntnu.edu.tw
B. Gopula, C.-W. Chiang, W.-Z. Lee, T.-S. Kuo, P.-Y. Wu, J. P. Henschke, H.-L. Wu, Org. Lett., 2014, 16, 632-635.
DOI: 10.1021/ol4035897
Abstract
N-tosyl aryl aldimines can be used as substrates in a rhodium-catalyzed enantioselective 1,2-addition reaction using alkenylboron nucleophiles. Addition of various potassium alkenyltrifluoroborates to aryl aldimines furnished the corresponding chiral allylic amines in good yield and high ee. This method efficiently provides di-, tri-, and tetrasubstituted allylic N-tosyl amines with high asymmetric induction.
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Key Words
ID: J54-Y2014
