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. 2015 Sep 18;20(9):17208–17220. doi: 10.3390/molecules200917208

Table 2.

Three-component reaction of anilines, ethyl glyoxalate, and epoxides a.

graphic file with name molecules-20-17208-i002.jpg

Entry 3 R1 R2 Yield (%) b d.r. c ee (%) d
1 3a CH3O CH2Cl 52 12:1 43
2 3b Cl CH2Cl 50 10:1 69
3 3c CH3CH2O CH2Cl 47 10:1 39
4 3d CH3O CH2OCH(CH3)2 56 4:1 43
5 3e CH3O CH2O(CH2)3CH3 46 1.5:1 71
6 3f CH3CH2O CH2O(CH2)3CH3 53 3:1 34
7 3g CH3CH2O CH2OCH(CH3)2 53 3:1 72
8 3h Cl CH2O(CH2)3CH3 48 3:1 69
9 3i Cl CH2OCH(CH3)2 54 4:1 90
10 3j CH3O Ph 42 1.7:1 84.6
11 3k NO2 CH2Cl trace ― ―

a Reactions were carried out under optimum conditions; b Yields of isolated products; cdetermined by 1H-NMR; d determined by HPLC on a chiral column.