Skip to main content
. 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 3.

[3+2] Cycloaddition ofstyrene (2a) with bicyclic cyclopropylamines 5.[a]graphic file with name nihms-362830-t0013.jpg

Entry Substrate Product[b] t [h] Yield [%][c]
d.r.[d]
1 graphic file with name nihms-362830-t0014.jpg graphic file with name nihms-362830-t0015.jpg 5 77
4:1
2 graphic file with name nihms-362830-t0016.jpg graphic file with name nihms-362830-t0017.jpg 8 74
5:1
3 graphic file with name nihms-362830-t0018.jpg graphic file with name nihms-362830-t0019.jpg 36 69
5:1
4 graphic file with name nihms-362830-t0020.jpg graphic file with name nihms-362830-t0021.jpg 12 28 (64)[e]
>25:1
5 graphic file with name nihms-362830-t0022.jpg graphic file with name nihms-362830-t0023.jpg 6 72
3:1
6 graphic file with name nihms-362830-t0024.jpg graphic file with name nihms-362830-t0025.jpg 12 58
4:1
[a]

Reaction conditions: 5a–f (0.2 mmol, 0.1m in degassed CH3NO2), 2a (1 mmol), 4a (2 mol%), irradiation with a 13 W fluorescent lightbulb at RT.

[b]

Only the major diastereoisomer shown.

[c]

Combined yields of the two isomers after chromatography.

[d]

Determined by 1H NMR analysis of the crude products (α/β).

[e]

Based on recovered 5d.