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. Author manuscript; available in PMC: 2010 Sep 17.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Sep 3;49(37):6589–6591. doi: 10.1002/anie.201002972

Table 1.

Optimization of reaction conditions.[a]

graphic file with name nihms-228349-f0006.jpg
Entry Imine (R1) Solvent Yield [%][b] ee [%][c]
1 2a (Ph) toluene 4a: 88 75
2 2a CH2Cl2 4a: 88 79
3 2a THF 4a: 86 47
4 2a EtOAc 4a: 93 84
5 2a iPrOAc 4a: 84 86
6 2b (4-MeOC6H4) iPrOAc 4b: 83 90
7 2c (2-MeC6H4) iPrOAc 4c: 92 84
8 2d (3-MeC6H4) iPrOAc 4d: 83 88
9 2e (3-MeOC6H4) iPrOAc 4e: 82 97
10 2 f (3,5-(MeO)2C6H3) iPrOAc 4 f: 81 96
[a]

Reaction conditions: imine 2a–f (0.1 mmol), hydroperoxide 3a (0.2 mmol), (R)-1 (5 mol%), solvent (0.6 mL) at room temperature.

[b]

Yield of isolated product.

[c]

Determined by HPLC analysis using a chiral stationary phase.