Table 3.

Assessment of nitrogen nucleophiles

Entry[a]	HNuc	Time	Product	Major enantiomer[b]	ee[c]
1	HN3[d]	60 m	4a	R	35
2	H2NBoc	24 h	5a	S	27
3	H2NNHBoc	14 d	6	S	65
4	H2NPh	14 d	7	S	30

^[a]Conditions: 0.05 mmol 3a, 0.0025 mmol precatalyst, 0.006 mmol AgOTf, 0.15 mmol nucleophile, 1.0 mL CDCl₃ (0.05 M).

^[b]Determined by optical rotation and comparison to literature precedents (see Supporting Information for details)

^[c]Determined by chiral HPLC.

^[d]Generated in situ from TMSN₃ (0.15 mmol) and TFA (0.10 mmol).