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. Author manuscript; available in PMC: 2013 Feb 6.
Published in final edited form as: Angew Chem Int Ed Engl. 2012 Jan 3;51(6):1405–1407. doi: 10.1002/anie.201107877

Table 2.

Substrate Scope of the Intramolecular Amination of Allylic Alcohols (0.6 M) Catalyzed by a 1:2 Mixture of [(S)-2](AuCl)2 (2.5 mol %) and AgClO4 (5 mol %) in Dioxane at 25 °C for 48 h.[18]

entry substrate heterocycle yield [%][a] ee [%][b]
1 graphic file with name nihms365050t2.jpg
(Z)-1g
graphic file with name nihms365050t3.jpg
3g
95 Š5
graphic file with name nihms365050t4.jpg graphic file with name nihms365050t5.jpg
2 (R = Me) 94 90
3 [R-R = –(CH2)5–] 95 94
4 graphic file with name nihms365050t6.jpg graphic file with name nihms365050t7.jpg 89 62
5 graphic file with name nihms365050t8.jpg
4 (R = Ph)
graphic file with name nihms365050t9.jpg
5
87[c] 90/92
6 (R = i-Pr) 98[c] 85/91
7 graphic file with name nihms365050t10.jpg graphic file with name nihms365050t11.jpg 87[c] 88/90
8 graphic file with name nihms365050t12.jpg graphic file with name nihms365050t13.jpg 69 77
9[d] (R1 = Fmoc, R2 = Boc) 86 94
10[d] (R1 = Fmoc, R2 = Ts) 99 92
11[d] (R1 = Boc, R2 = Fmoc) 99 91
[a]

Isolated yield.

[b]

Determined by HPLC analysis on chiral support.

[c]

Diastereomeric ratio = ~1:1.

[d]

Reaction run at 50 °C.