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: ymli
nankai.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
see article for more reactions
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.
see article for more examples
Regioselective (Diacetoxyiodo)benzene-Promoted Halocyclization of Unfunctionalized Olefins
G.-Q. Liu, Y.-M. Li, J. Org. Chem., 2014, 79, 10094-10109.
Key Words
ID: J42-Y2016
