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. Author manuscript; available in PMC: 2017 May 10.
Published in final edited form as: Angew Chem Int Ed Engl. 2016 Apr 20;55(20):6079–6083. doi: 10.1002/anie.201601550

Table 5.

Substrate Scope of hydroazidation and hydroamination

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Entry[a],[b] 3 Ar 4, yield[c], ee[d] 5, yield[c], ee[d]
1 3a Ph 4a, 92, 90 5a, 89, 89
2 3b 4-MeC6H4 4b, 89, 84 5b, 82, 80
3 3c 4-SiMe3C6H4 4c, 67, 74 5c, 56, 73
4 3d 4-PhC6H4 4d, 84, 84 5d, 49, 64
5 3e 4-FC6H4 4e, 86, 86 5e, 75, 87
6 3f 4-BrC6H4 4f, 88, 90 5f, 84, 92
7 3g 4-CF3C6H4 4g, 41, 74 5g, 97, 92
8 3h 3-MeC6H4 4h, 89, 85 5h, 63, 83
9 3i 3-OMeC6H4 4i, 65, 84 5i, 82, 78
10 3j 3-PhC6H4 4j, 92, 89 5j, 74, 72
11 3k 3-BrC6H4 4k, 87, 88 5k, 77, 85
12 3l 2-MeC6H4 4l, 81, 62 5l, 74, 80
13 3m 3-thienyl 4m, 86, 75 5m, 71, 77
[a]

Condition A: 0.1 mmol 3, 0.005 mmol A5·(AuCl)2, 0.015 mmol AgOTf, 0.3 mmol TMSN3, 0.2 mmol H2O, in 2.0 mL of THF:CHCl3 (3:1 v/v, 0.05M), 72 h at −10 °C. Condition B: 0.05 mmol 3, 0.0025 mmol A4·(AuCl)2, 0.006 mmol AgOTf, 0.15 mmol tert-butyl carbamate, in 1.0 mL of 1,4-dioxane (0.05M), 24 h at rt.

[b]

Absolute stereochemistry assigned by analogy to 4a and 5a.

[c]

Isolated yield.

[d]

Determined by chiral HPLC.