Table 1. Screening between the Organocatalyst and the Supramolecular Catalyst in the Aldol Reaction^a.

entry	solvent/gel/xerogel (mL)	time (h)	yield (%)b	drc [anti/syn]	ee (%)d [anti]
1	H2O (0.01)	3	95	83/17	64
2	H2O (0.1)	3	93	91/9	36
3	H2O (0.5)	3	94	91/9	66
4	H2O (1)	3	95	60/40	64
5e	H2O (0.5)	3	92	83/17	70
6	brine (0.5)	2	96	90/10	60
7	H2O (0.1)	3	91	88/12	82
8	H2O (0.5)	9	89	87/13	78
9	H2O (1)	3	92	88/12	80
10	brine (0.5)	15	90	89/11	84
11	DCM	6	85	63/37	22
12f	gel	36	89	78/22	64
13g	xerogel	2	94	84/16	86
14h	xerogel	2	95	93/7	95
15i	xerogel	2	93	89/11	94
16j	xerogel	2	94	84/16	95
17	xerogel	2	94	83/17	88

^aReactions were carried out by using aldehyde (1 mmol), cyclohexanone (4 mmol), catalyst (0.02 mmol), and benzoic acid (0.02 mmol) in 0.1 mL of water at room temperature for the mentioned time. Entries 1–6 are examples with the L–L isomer of the organocatalyst, and entries 7–10 are examples with the L–D isomer of the organocatalyst. Entries 11–16 are examples in the presence of the supramolecular catalyst.

^bIsolated yield after purification by column chromatography.

^cAnti/syn diastereomeric ratios were determined by ¹H NMR spectrum of the crude product mixture.

^dDetermined by chiral HPLC analysis (chiral phases: Chiralpak OD-H, AD-H and AS-H) with hexane–IPA as an eluent.

^e5 mol % catalyst was used.

^fWithout evaporation of the solvent from the gel.

^gXerogel obtained from acetonitrile.

^hXerogel obtained from the acetonitrile/chloroform mixture.

ⁱXerogel obtained from the acetonitrile/DCM mixture.

^jXerogel obtained from the acetonitrile/THF mixture.