Table 11.

Catalytic ligand-mediated addition of MeLi to imines 8–11

entry	R1	imine	ligand	temp, °C	product	yield, %a	erb
1	Ph	8	12ba	−78	15	27	68.5:31.5
2	Ph	8	12bb	−78	15	30	81.5:18.5
3	Ph	8	12bc	−78	15	46	83.0:17.0
4	Ph	8	12bc	−63	15	66	84.0:16.0
5	Ph	8	12bc	−41	15	97	84.5:15.5
6	Ph	8	12be	−78	15	12	77.5:22.5
7	Ph	8	12be	−63	15	51	81.0:19.0
8	Ph	8	12be	−41	15	99	81.5:18.5
9	Ph	8	12cc	−63	15	23	84.0:16.0
10	Ph	8	12cc	−41	15	83	77.0:23.0
11	1–naphthyl	9	12bc	−63	18	44	84.0:16.0
12	1–naphthyl	9	12bc	−41	18	97	80.0:20.0
13	PhCH=CH	10	12bc	−63	17	30	90.0:10.0
14	PhCH=CH	10	12bc	−41	17	92	84.0:16.0
15	PhCH=CH	10	12cc	−41	17	92	77.5:22.5
16	PhCH2CH2	11	12bb	−63	16	45	70.5:29.5
17	PhCH2CH2	11	12bc	−78	16	41	90.0:10.0
18	PhCH2CH2	11	12bc	−63	16	52	89.5:10.5
19	PhCH2CH2	11	12bc	−41	16	64	78.0:22.0

^aYield of chromatographically homogeneous material.

^bAll compounds have R configuration. Determined by CSP-HPLC analysis.