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. Author manuscript; available in PMC: 2012 Apr 20.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Nov 23;51(1):222–226. doi: 10.1002/anie.201106162

Table 2.

[3+2] Cycloaddition of styrene (2a) with monocyclic cyclopropylamines (1).[a]graphic file with name nihms-362830-t0003.jpg

Entry Substrate Product t [h] Yield [%][d]
1[b] 1a, R=H graphic file with name nihms-362830-t0004.jpg 3 87
2[b] 1b, R=4-CI graphic file with name nihms-362830-t0005.jpg 6 82
3[b] 1c, R=4-CF3 graphic file with name nihms-362830-t0006.jpg 4 82
4[c] graphic file with name nihms-362830-t0007.jpg graphic file with name nihms-362830-t0008.jpg 24 80
5[c] graphic file with name nihms-362830-t0009.jpg graphic file with name nihms-362830-t0010.jpg 6 75
6[b] graphic file with name nihms-362830-t0011.jpg graphic file with name nihms-362830-t0012.jpg 48 71
[a]

Reaction conditions: substrate (0.2 mmol, 0.1m in degassed CH3NO2), 2a (1 mmol), 4a (2 mol%), irradiation with a 13 W fluorescent lightbulb at RT.

[b]

d.r.=1:1

[c]

d.r.=3:2 as determined by 1H NMR spectroscopy of crude products.

[d]

Yield of the combined isomers after isolation.