Table 2.

Scope of Enantioselective Hydroamination^a

entry	R	R1	product	time (h)	temp (d°C)	yieldb	eec
1	C6H5	Me	2a	12	3	83	94
2d	C6H5	Me	2a	72	3	79	92
3	p-ClC6H4	Me	2b	5	3	87	95
4	p-(Me)C6H4	Me	2c	36	3	84	87
5	p-(OMe)C6H4	Me	2d	96	3	96	91
6	o-ClC6H4	Me	2e	5	3	91	92
7	m-ClC6H4	Me	2f	5	3	87	94
8	C6H5	-CH2(CH2)3CH2-	2g	5	3	82	96
9	C6H5	H	2h	72	30	68	81
10	p-ClC6H4	H	2i	36	30	93	83
11	H	Me	2j	2	3	86	78
12e	H	Me	2j	2	3	91	85

^aReactions were performed on a 0.18–0.25 mmol scale, and were quenched by the addition of p-NO₂ benzoyl chloride. For entries 1–3, 6–8, and 11–12 the hydroxylamine was generated in situ from the corresponding trifluoroacetate salt by addition of aqueous potassium carbonate.

^bIsolated yields of O-benzoylated products after purification on silica gel.

^cDetermined by HPLC analysis of O-benzoylated products using commercial chiral columns.

^dmol% of 5 was used.

^e10 mol% of 3e was used as the catalyst.