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Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A

Pei-Fen Chiang, Wei-Sian Li, Jia-Hong Jian, Ting-Shen Kuo, Ping-Yu Wu and Hsyueh-Liang Wu*

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

P. F. Chiang, W.-S. Li, J.-H. Jiang, T.-S. Kuo, P.-Y. Wu, H.-L. Wu, Org. Lett., 2018, 20, 158-161.

DOI: 10.1021/acs.orglett.7b03523 (free Supporting Information)


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Abstract

An asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines with potassium allyltrifluoroborates generataes enantioenriched homoallylic amines in very good yields with very good enantioselectivities. Using subsituted allyltrifluoroborates, high diastereoselectivity is achieved. Reactions of both potassium (E)- and (Z)-crotyltrifluoroborates provide the same diastereomer.

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Total synthesis of (-)-Crispine A



Key Words

homoallylic amines


ID: J54-Y2018