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Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C-Aliphatic Homoallylic Amines

Wei-Sian Li, Ting-Shen Kuo, Meng-Chi Hsieh, Ming-Kang Tsai, 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

W.-S. Li, T.-S. Kuo, M.-C. Hsieh, M.-K. Tsai, P.-Y. Wu, H.-L. Wu, Org. Lett., 2020, 22, 5675-5679.

DOI: 10.1021/acs.orglett.0c02069 (free Supporting Information)



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Abstract

A Rh-catalyzed asymmetric allylation of aliphatic aldimines provides optically active 1-alkyl homoallylic amines in good yields and very good ee under mild, aqueous reaction conditions. The preparation of indolizidine and piperidine alkaloids demonstrates the usefulness of this method.

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Key Words

Homoallylic Amines


ID: J54-Y2020