Table 13.

(−)–Sparteine–promoted addition of organolithium reagents to imine 11

entry	ligand	amount	R2	solvent	temp, °C	product	yield, %a	erb
1	12bc	1.0	Me	toluene	−63	16	83	94.5:5.5
2	4	1.0	Me	toluene	−78	16	71	86.0:14.0
3	4a	1.0	Me	toluene	−78	16	79	70.0:30.0
4	12bc	1.0	n-Bu	toluene	−78	19	82	78.5:21.5
5	12bc	1.0	n-Bu	i-Pr2O	−78	19	86	84.5:15.5
6	12bc	1.0	n-Bu	Et2O	−78	19	90	76.5:23.5
7	4	1.0	n-Bu	toluene	−94	19	86	89.5:10.5
8	4	1.0	n-Bu	i-Pr2O	−78	19	85	91.5:8.5
9	4	1.0	n-Bu	Et2O	−94	19	90	95.5:4.5
10	12bc	0.2	n-Bu	i-Pr2O	−78	19	92	75.5:24.5
11	4	0.2	n-Bu	Et2O	−78	19	91	89.5:10.5
12	12bc	1.0	Ph	toluene	−78	20	82	65.0:35.0
13	4	1.0	Ph	toluene	−94	20	99	91.0:9.0
14	4	1.0	Ph	i-Pr2O	−78	20	71	85.0:15.0
15	4	1.0	Ph	Et2O	−78	20	85	81.0:19.0
16	4	0.1	Ph	Et2O	−78	20	86	56.5:43.5
17	4	0.2	Ph	toluene	−78	20	97	69.5:30.5

^aYield of chromatographically homogeneous material.

^bDetermined by CSP-HPLC analysis.