Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 12, Pages 5144-5161Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00725
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Funding
- National Natural Science Foundation of China [NSFC 21272121]
- Nankai University [68140001]
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A general and practical method for the preparation of trans-2-substituted-4-halopiperidines and cis-2,substituted-4-halotetrahydropyrans is reported. Using 5 mol % of AlCl3 as the catalyst and 2 equiv of trimethylsilyl halides as the halide sources, aza-Prins cyclization of N-tosyl homoallylamine or-Prins cyclization of homoallylic alcohol with carbonyl compounds could be readily realized, giving the corresponding trans-2-substituted-4-halopiperidines or cis-2-substituted-4-halotetrahydropyrans in high yields and satisfactory diastereoselectivity.
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