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. Author manuscript; available in PMC: 2009 Sep 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2008;47(38):7358–7362. doi: 10.1002/anie.200802910

Table 3.

Catalytic ACA reactions of trialkyl aluminum reagents with cyclohexenones and cycloheptenones promoted by NHC copper complexes.[a]

graphic file with name nihms110606t3.jpg

Entry Substrate [R] (alkyl)3Al NHC–AgI T [°C] t [h] Yield [%][b] e.r.[c] ee [%][c]
1 [d] 8a [Me] iBu3Al 4 22 0.25 89 95:5 90
2 8b [5-hexenyl] Me3Al 5 −78 12 85 95:5 90
3 8c [CO2Me] Et3Al 3 −78 6 91 91.5:8.5 83
4 9a [nBu] Me3Al 5 −78 12 90 92.5:7.5 85
5 9a [nBu] Et3Al 5 22 0.25 87 94.5:5.5 89
[a–c]

See Table 2.

[d]

5 mol % CuCl2·2 H2O was used.