Table 2.

Optimization of amines for palladium/enamine catalysis^a

Entry	[Pd]	[Amine]	Sol.	Conv.b	Yieldb	ee%c
1d	Pd(OAc)2	n/a	MeCN	<5%	<5%	-
2	Pd(OAc)2	A1	Tol	100%	95%	-
3	Pd(OAc)2	A2 or A3	Tol	<20%	<20%	0
4	Pd(OAc)2	A4	Tol	62%	54%	11%
5	Pd(CH3CN)2Cl2	A4	Tol	79%	77%	15%
6	Pd(CH3CN)2Cl2	A5	Tol	100%	90%	33%
7	Pd(CH3CN)2Cl2	A6	Tol	100%	91%	63%
8	Pd(CH3CN)2Cl2	A7	Tol	100%	57%	<5%
9	Pd(CH3CN)2Cl2	A8	Tol	100%	96%	65%
10	Pd(CH3CN)2Cl2	A9	Tol	100%	97%	71%
11e	Pd(CH3CN)2Cl2	A9	Tol	100%	97%	<5%
12f	Pd(CH3CN)2Cl2	A9	Tol	60%	55%	93%
13f	Pd(CH3CN)2Cl2	A9	neat	100%	99% (95%)g	88%

^aReaction conditions: [Pd] cat. (10 mol%), [amine] cat. (30 mol%), AcOH (1 eq.), solvent (0.5 M), under 80 °C, 24 hours.

^bConversion and yield were determined by ¹H NMR using 1,3,5-trimethoxybenzene as internal standard.

^cee value was determined by HPLC.

^d120 °C, 36 hours.

^e72 h.

^f60 °C, 24 hours.

^gIsolated yield.