Table 2. Enantioselective addition of phenylacetylene to aromatic imines in toluene.

Entry	Aldehyde	Aniline	Temperature, °C/time, days	Yield, %	OR/ee %
1	PhCHO	PhNH2	22/4	78	(+) 96
2	PhCHO	PhNH2	35/2	83	(+) 93
3	4-CH3C6H4CHO	PhNH2	35/2	85	(+) 92
4	4-C2H5C6H4CHO	PhNH2	22/4	70	(+) 96
5	4-C2H5C6H4CHO	PhNH2	35/2	73	(+) 95
6	4-ClC6H4CHO	PhNH2	22/4	85	(+) 94
7	4-ClC6H4CHO	PhNH2	35/2	90	(+) 92
8	4-BrC6H4CHO	PhNH2	22/4	87	(+) 94
9	4-BrC6H4CHO	PhNH2	35/2	90	(+) 92
10	3-BrC6H4CHO	PhNH2	22/4	85	(+) 95
11	3-BrC6H4CHO	PhNH2	35/2	88	(+) 92
12	4-PhC6H4CHO	PhNH2	22/4	81	(+) 94
13	4-PhC6H4CHO	PhNH2	35/2	85	(+) 90
14	2-NaphCHO	PhNH2	22/4	63	(+) 88
15	2-NaphCHO	PhNH2	35/2	67	(+) 82
16	4-CF3C6H4CHO	PhNH2	22/4	71	(+) 93
17	PhCHO	4-BrC6H4NH2	35/2	93	(+) 91
18	PhCHO	4-ClC6H4NH2	35/2	92	(+) 91
19	PhCHO	4-CH3C6H4NH2	35/2	93	(+) 94

OR, optical rotation.