Table 2. Henry Reaction Catalyzed by Ligands 3a–3d.

entry	R	3	yield (%)b	ee (%)c	9
1	H	3a	77	57	9a
2d	H	3a	75	56	9a
3	H	3b	44	0	9a
4	H	3c	90	75	9a
5	H	3d	87	91	9a
6	2-Cl	3a	71	47	9b
7	2-Cl	3c	90	74	9b
8	2-Cl	3d	90	70	9b
9	2-MeO	3a	43	39	9c
10d	2-MeO	3c	85	80	9c
11d	2-MeO	3d	67	84	9c
12	2-Me	3a	59	49	9d
13	2-Me	3c	90	89	9d
14	2-Me	3d	77	79	9d
15	4-Me	3a	47	47	9e
16	4-Me	3c	65	88	9e
17	4-Me	3d	36	84	9e
18	3-Me	3a	58	44	9f
19	3-Me	3c	72	84	9f
20	3-Me	3d	72	84	9f
21	4-CN	3a	60	36	9g
22	4-CN	3c	90	50	9g
23	4-CN	3d	>95	48	9g
24	3-NO2	3a	65	37	9h
25	3-NO2	3c	>95	53	9h
26	3-NO2	3d	83	33	9h

^aAll experiments were performed under identical conditions unless otherwise stated: 2-PrOH, 10 mol % of 3, 10 mol % of Cu(OAc)₂, rt, 72 h.

^bDetermined by NMR analysis.

^cDetermined by chiral HPLC analysis.

^dNanoparticles previously treated with hexamethyldisilazane were used (see Experimental Section).