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. Author manuscript; available in PMC: 2017 Apr 5.
Published in final edited form as: Org Lett. 2015 Aug 11;17(16):3975–3977. doi: 10.1021/acs.orglett.5b01919

Table 3.

Scope of the Aza-Prins Fluorocyclizationa

graphic file with name nihms829365u4.jpg

entry R time (h) 5 yield (%) cis-5/trans-5b
1 cyclohexyl– 4 5a 100 10:1
2 n-C5H11 4 5b 100 8.5:1
3 Ph– 24 5c 96 2:1
4 4-Br-C6H4 24 5d 90 2.5:1
5 4-NO2C6H4 24 5e 42 2:1
6 4-MeOC6H4 48 5f 0
a

4 (0.2 mmol), 2 (0.2 mmol), and DMPU/HF (2.1 mmol of HF) in DCE (0.5 mL) was mixed in a polyethylene vial and then stirred at 55 °C.

b

Determined by 19F NMR.

c

Room temperature.

d

Determined by 19F NMR using PhCF3 as internal standard.