Table 2. Substituent Effects of Different Aromatic Aldehydes and Ketones in the Aldol Reaction^a.

entry	aryl	R1 R2	time (h)	yield (%)b	drc [anti/syn]	ee (%)d [anti]
1	4-NO2C6H4	(CH2)3	2	92	93/7	95
2	2-MeOC6H4	(CH2)3	6	89	89/11	93
3	2-ClC6H4	(CH2)3	2	97	99/1	91
4	3-CNC6H4	(CH2)3	4	91	93/7	92
5	4-BrC6H4	(CH2)3	3	92	92/8	94
6	2-NO2C6H4	(CH2)3	1.5	96	93/7	94
7	2-FC6H4	(CH2)3	1.5	95	95/5	92
8	3-FC6H4	(CH2)3	2.5	91	96/4	94
9	4-CF3C6H4	(CH2)3	2	94	95/5	90
10	2-naphthyl	(CH2)3	8	92	93/7	92
11	3-MeOC6H4	(CH2)3	4	93	92/8	90
12	4-MeC6H4	(CH2)3	6	90	85/15	82
13	4-NO2C6H4	CH2OCH2	1.5	95	88/12	95
14	4-NO2C6H4	CH2CHMeCH2	1.5	93	88/12	90
15	4-NO2C6H4	(CH2)2	2	95	87/13	>99
16	4-NO2C6H4	CH2SCH2	7	97	85/15	80
17	4-NO2C6H4	CH2NBocCH2	3	89	61/39	65
18e	4-NO2C6H4	(CH2)3	4	82	94/6	85
19e	2-MeOC6H4	(CH2)3	48	64	88/12	88
20e	2-ClC6H4	(CH2)3	30	71	92/8	87
21e	3-CNC6H4	(CH2)3	24	81	94/6	89

^aReactions were carried out by using aldehyde (1 mmol), cyclohexanone (4 mmol), supramolecular catalyst (0.02 mmol), and benzoic acid (0.02 mmol) in 0.1 mL of water at room temperature for the mentioned time.

^bIsolated yield after purification by column chromatography.

^cDiastereomer ratios (anti/syn) 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.

^eReaction performed with the L–D isomer.