Table 1.

Optimization of coupling of ketimine 1a and allyl phenyl ether 2a^a,b.

Entry	Base (equiv.)	Solvent	Conc.	Assay yield (%)
1	NaN(SiMe3)2 (3.0)	MTBE	0.2 M	64
2	NaN(SiMe3)2 (3.0)	DME	0.2 M	10
3	NaN(SiMe3)2 (3.0)	CPME	0.2 M	74
4	NaN(SiMe3)2 (3.0)	THF	0.2 M	20
5	NaN(SiMe3)2 (3.0)	Dioxane	0.2 M	0
6	NaN(SiMe3)2 (3.0)	DMSO	0.2 M	0
7	NaN(SiMe3)2 (3.0)	DMF	0.2 M	0
8	NaN(SiMe3)2 (3.0)	Toluene	0.2 M	84
9	LiOtBu (3.0)	Toluene	0.2 M	0
10	NaOtBu (3.0)	Toluene	0.2 M	0
11	KOtBu (3.0)	Toluene	0.2 M	0
12	LiN(SiMe3)2 (3.0)	Toluene	0.2 M	23
13	KN(SiMe3)2 (3.0)	Toluene	0.2 M	8
14	NaN(SiMe3)2 (2.0)	Toluene	0.2 M	74
15	NaN(SiMe3)2 (4.0)	Toluene	0.2 M	89 (86)c
16d	NaN(SiMe3)2 (4.0)	Toluene	0.2 M	73
17e	NaN(SiMe3)2 (4.0)	Toluene	0.2 M	70
18	NaN(SiMe3)2 (4.0)	Toluene	0.1 M	63

^aReaction conditions: 1a (0.2 mmol, 2.0 equiv.), 2a (0.1 mmol, 1.0 equiv.), room temperature, 12 h.

^bAssay yields determined by ¹H NMR spectroscopy of the crude reaction mixtures using CH₂Br₂ as an internal standard.

^cIsolated yield.

^d1a (1.5 equiv.).

^e6 h.

MTBE methyl tert-butyl ether, DME dimethoxyethane, CPME cyclopentyl methyl ether, THF tetrahydrofuran, DMSO dimethyl sulfoxide, DMF N,N-dimethylformamide.