Table 12.

Catalytic addition of organolithium reagents to imine 11

entry	R2	12bc, equiv	solvent	product	temp, °C	yield, %a	erb
1	Me	0.1	toluene	16	−78	41	90.0:10.0
2	Me	0.1	toluene	16	−63	52	89.5:10.5
3	Me	0.2	toluene	16	−63	97	91.5:8.5
4	n-Bu	0.1	toluene	19	−78	62	59.0:41.0
5	n-Bu	0.1	toluene/Et2O, 8:1	19	−78	86	72.0:28.0
6	n-Bu	0.1	i-Pr2O	19	−78	81	70.5:29.5
7	n-Bu	0.2	i-Pr2O	19	−78	92	75.5:24.5
8	CH2=CH	0.1	toluene	21	−78	49	83.0:17.0
9	CH2=CH	0.2	toluene	21	−78	82	91.0:9.0

^aYield of chromatographically homogeneous material.

^bDetermined by CSP-HPLC analysis.