Table 2.

Optimization of iridium-catalyzed allylic alkylation reaction of alkyl-substituted electrophile 43^a

Entry	L	Base (200 mol %)	Additive (mol %)	LG	yield (%)b	b:lc	drc	ee (%)d
1	L6	-	LiBr (100)	OCO2Me	100	55:45	6.4:1	-
2	L6	LiOt-Bu	-	OCO2Me	85	34:66	5.3:1	-
3	L6	LiOt-Bu	LiCI (100)	OCO2Me	69	50:50	7.2:1	-
4	L6	LiOt-Bu	LiCI (100)	CI	94	86:14	4.8:1	-
5	L6	Proton sponge	LiCI (100)	CI	100	93:7	7.9:1	66
6	L7	Proton sponge	LiCI (100)	CI	46	95:5	6.0:1	96
7	L7	Proton sponge	LiCI (400)	Cl	78	94:6	6.7:1	97

^aReactions performed on 0.1 mmol of 43, 0.2 mmol of 24 in THF (0.1 M) for 18 h.

^b1H NMR yield of the mixture of diastereomers based on internal standard.

^cDetermined by ¹H NMR analysis of the crude reaction mixture.

^dDetermined by chiral SFC analysis.

^eProton sponge = 1,8-bis(dimethylamino)naphthalene.