Table 4.

Substrate Scope of the Catalytic Asymmetric 3-Component Ugi Reaction.^a

entry	series	R	time (h)	temp (°C)	% yield 3b	erc
1	a	C6H5	7	40	87e	86 : 14
2d	a	C6H5	24	25	86 (71)	90 : 10 (>99.5 : 0.5)
3	a	C6H5	66	0	75	92 : 8
4f	b	4-NO2C6H4	24	25	83	93 : 7
5f	b	4-NO2C6H4	66	0	51e	92 : 8
6	c	4-CF3C6H4	24	25	85	91 : 9
7	d	4-BrC6H4	24	25	85	93 : 7
8	d	4-BrC6H4	48	0	65g	95 : 5
9f	d	4-BrC6H4	48	0	75h,i	95 : 5
10f	e	3-BrC6H4	22	25	82	93 : 7
11	e	3-BrC6H4	66	0	66h	92 : 8
12	f	3,4-Cl2C6H3	24	25	85	94 : 6
13	f	3,4-Cl2C6H3	66	0	54e	95 : 5
14	g	4-FC6H4	24	25	87e	91 : 9
15	g	4-FC6H4	67	0	62	94 : 6
16	h	4-MeO2CC6H4	24	25	80	93 : 7
17f	h	4-MeO2CC6H4	67	0	62	93 : 7
18	i	4-OAcC6H4	24	25	86	85 : 15
19	j	4-AcNHC6H4	24	25	77 (47)	85 : 15 (96:4)
20f	k	4-MeC6H4	24	25	84 (47)	91 : 9 (>99.5 : 0.5)
21	k	4-MeC6H4	66	0	80e	92 : 8
22	l	2-MeC6H4	24	25	76 (56)	78 : 22 (>99 : 1)
23	m	4-t-BuC6H4	24	25	83	84 : 16
24	n	4-MeOC6H4	40	25	84j	88 : 12
25	n	4-MeOC6H4	24	25	70	89 : 11
28	n	4-MeOC6H4	24	0	51	92 : 8
27	o	3-pyridyl	25	25	80 (61)	90 : 10 (>99 : 1)
28	p	4-pyridyl	70	25	66	89 : 11

^aUnless otherwise specified, all reactions were carried out at 0.2 M in 1 (0.25 mmol) in mesitylene with 2.0 equiv amine and 1.5 equiv of 2 at rt in the presence of 4Å MS for the indicated time with 20 mol% of the catalyst. The catalyst was made from the (R)-enantiomer of the ligand (≥99% ee) according to the procedure in Table 1.

^bIsolated yield after chromatography on silica gel. Yield in paranthesis is % recovery of the first crop after crystallization

^cDetermined by HPLC. The er in parentheses is of the first crop.

^dAverage of 4 runs.

^e1H NMR yield with internal standard (Ph₃CH).

^fAverage of 2 runs.

^gYield was 46% after 24 h.

^hReaction at 0.4 M.

ⁱYield was 76% after 66 h. The yield was 60% after 66 h in the absence of 4Å MS.

^jRun in the absence of 4Å MS.