Table 3. Enantioselective addition of phenylacetylene to aromatic imines in water.

Entry	Aldehyde	Aniline	Temperature, °C/time, days	Yield, %	OR/ee %
1	PhCHO	PhNH2	22/4	71	(+) 84
2	PhCHO	PhNH2	35/2	77	(+) 80
3	4-CH3C6H4CHO	PhNH2	35/2	86	(+) 81
4	4-C2H5C6H4CHO	PhNH2	22/4	68	(+) 89
5	4-C2H5C6H4CHO	PhNH2	35/2	68	(+) 78
6	4-ClC6H4CHO	PhNH2	22/4	70	(+) 87
7	4-ClC6H4CHO	PhNH2	35/2	74	(+) 85
8	4-BrC6H4CHO	PhNH2	22/4	63	(+) 87
9	4-BrC6H4CHO	PhNH2	35/2	74	(+) 85
10	3-BrC6H4CHO	PhNH2	22/4	69	(+) 85
11	3-BrC6H4CHO	PhNH2	35/2	72	(+) 82
12	4-PhC6H4CHO	PhNH2	22/4	48	(+) 84
13	4-PhC6H4CHO	PhNH2	35/2	56	(+) 82
14	2-NaphCHO	PhNH2	22/4	57	(+) 86
15	2-NaphCHO	PhNH2	35/2	65	(+) 78
16	4-CF3C6H4CHO	PhNH2	22/4	56	(+) 87
17	PhCHO	4-BrC6H4NH2	35/2	82	(+) 83
18	PhCHO	4-ClC6H4NH2	35/2	77	(+) 84
19	PhCHO	4-CH3C6H4NH2	35/2	68	(+) 91