Table 3.

Catalytic diastereo- and enantioselective additions to N-H ketimines.

Entry	G	Mol %; Yield (%)†	e.r.††
1	C6H5 (a)	7.5; 76	95:5
2	o-MeOC6H4 (b)	10; 95	98.5:1.5
3	o-ClC6H4 (c)	7.5; 91	99.5:0.5
4	o-FC6H4 (d)	7.5; 72	97.5:2.5
5	o,o-F2C6H3 (e)	7.5; 91	98:2
6	1-naphthyl (f)	10; 66	98.5:1.5
7	o-MeC6H4 (g)	7.5; 59	99.5:0.5
8	m-FC6H4 (h)	5.0; 64	94:6
9	m-MeOC6H4 (i)	10; 57	98.5:1.5
10	2-naphthyl (j)	7.5; 81	93:7
11	p-ClC6H4 (k)	7.5; 56	92.5:7.5
12	p-FC6H4 (l)	5.0; 71	95:5
13	p-MeOC6H4 (m)	7.5; 39	92.5:7.5
14	CyCH2 (n)	10; 38	91:9
15	Cy (o)	10; 48	95:5

Reactions were carried out under N₂ atmosphere; >98% disappearance of ketimine in all cases (includes desired and decomposition products).

^†Yield of isolated and purified products (<±5%).

^††Enantiomeric ratios determined by HPLC analysis (<±1%; see the Supplementary Information for details).

Abbreviations: TBS, tert-butyldimethylsilyl; pin, pinacolato; Cy, cyclohexyl.

Experiments were performed at least in triplicate. See the Supplementary Information for details and the results with achiral imidazolinium salt 4c.