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. Author manuscript; available in PMC: 2009 Sep 30.
Published in final edited form as: J Am Chem Soc. 2008 Jun 25;130(29):9244–9245. doi: 10.1021/ja803890t

Table 2.

[4 + 3]-Cycloaddition of α,β-Unsaturated Imines

graphic file with name nihms-110691-t0008.jpg
entry imine azepine Yield
1 graphic file with name nihms-110691-t0009.jpg graphic file with name nihms-110691-t0010.jpg b Ar = 4-HO-2,6-Me2-C6H2 87%
2 c Ar = 2,6-Me2-C6H3 80%
3 d Ar = 2,3-Me2-C6H3 88%
4 e Ar = 4-MeO-C6H4 65%
5 f Ar = 4-F-C6H4 55%
6 graphic file with name nihms-110691-t0011.jpg graphic file with name nihms-110691-t0012.jpg a Ar = 4-NO2C6H4 70%
7 b Ar = 4-MeOC6H4 80%
8 graphic file with name nihms-110691-t0013.jpg graphic file with name nihms-110691-t0014.jpg 65%
9 graphic file with name nihms-110691-t0015.jpg graphic file with name nihms-110691-t0016.jpg 62%
10 graphic file with name nihms-110691-t0017.jpg graphic file with name nihms-110691-t0018.jpg 63%
a

Conditions: 1.3 equiv of 1, 5% 4, CH2 Cl2, rt. Ar’ = 4-HO-2,6-Me2-C6H2.