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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 1.

Effect of nucleophile on the gold(I)-catalyzed intramolecular amination of allylic alcohols (E)-1 under optimized conditions.[16,18]

graphic file with name nihms365050u1.jpg
entry R X time [h] pyrrolidine yield [%][a] ee [%][b]
1 Bn SbF6 5 3a 100[c] 29
2 Cbz ClO4 48 3b 99 79
3 Boc ClO4 48 3c 97 80
4[d] Troc ClO4 48 3d 62 84
5 CO2Me ClO4 48 3e 97 75
6 Ts ClO4 48 3f 98 76
7 Fmoc ClO4 48 3g 95 91
graphic file with name nihms365050t1.jpg
[a]

Isolated yield.

[b]

Determined by HPLC analysis on chiral support.

[c]

Conversion.

[d]

Reaction run at 40 °C.