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Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl3-Catalyzed Prins Reaction

Gong-Qing Liu, Bin Cui, Rong Xu and Yue-Ming Li*

*State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, People’s Republic of China, Email: ymlinankai.edu.cn

G.-Q. Liu, B. Cui, R. Xu, X.-M. Li, J. Org. Chem., 2016, 81, 5144-5161.

DOI: 10.1021/acs.joc.6b00725 (free Supporting Information)


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Abstract

The use of 5 mol % of AlCl3 as the catalyst and 2 equiv of a trimethylsilyl halide as the halide source enables aza-Prins cyclization of N-tosyl homoallylamine or Prins cyclization of homoallylic alcohol with carbonyl compounds to provide the corresponding trans-2-substituted-4-halopiperidines or cis-2-substituted-4-halotetrahydropyrans in high yields and satisfactory diastereoselectivity.


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Regioselective (Diacetoxyiodo)benzene-Promoted Halocyclization of Unfunctionalized Olefins

G.-Q. Liu, Y.-M. Li, J. Org. Chem., 2014, 79, 10094-10109.


Key Words

Piperidines, Prins Reaction


ID: J42-Y2016