Table 1.

Optimization of resolution of amino phenol 1^a

Entry	2	Cat	Solvent	Conv. (%)b	Product, ee (%)c	1a, ee (%)c	S d
1	2a	A	CH2Cl2	30	3a, 60	26	5
2	2a	B	CH2Cl2	26	3a, −26	−9	2
3	2a	C	CH2Cl2	76	3a, −7	−23	1.4
4e	2a	D	CH2Cl2	5	3a, 73	4	6.6
5	2a	E	CH2Cl2	28	3a, 74	29	9
6e	2a	F	CH2Cl2	9	3a, 78	8	8.7
7	2a	E	CH3CN	80	3a, 22	90	4
8	2a	E	THF	28	3a, 20	8	1.6
9	2a	E	EtOAc	28	3a, 36	14	2.4
10	2a	E	1:1 CH2Cl2/CH3CN	62	3a, 50	82	7
11f	2b	E	1:1 CH2Cl2/CH3CN	60	4a, 65	98	21
12g	2b	E	1:1 CH2Cl2/CH3CN	39	4a, 86	55	23

^aUnless noted otherwise, the reactions were performed with 1a (0.04 mmol, 1.0 equiv.), 2 (0.8 equiv.), catalyst (20 mol%) in solvent (0.5 mL) at 24 ^oC for 4 h

^bDetermined by ¹H NMR

^cDetermined by chiral HPLC

^dS = ln[(1 − Conv.)(1 − ee_1a)]/ln[(1 − Conv.)(1 + ee_1a)]

^e15 h instead of 4 h

^fThe reaction time was 24 h

^gUse of 10 mol% E and with 24 h reaction time