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. Author manuscript; available in PMC: 2015 Jul 6.
Published in final edited form as: J Am Chem Soc. 2015 May 4;137(18):5891–5894. doi: 10.1021/jacs.5b02887

Table 1.

Optimization of Reaction Conditions

graphic file with name nihms702042t1.jpg
Entry Azolium Temp. (°C) Additive (mol %) yield (%)a erb time (h)
1 A 23 none 80 66:34 12
2 A 23 HBD1 (30) 44 88:12 12
3 A 0 HBD1 (30) 41 93:7 12
4 A 0 HBD1 (30), DMAP (10) 71 92:8 10
5 B 0 HBD1 (30), DMAP (10) 40 84:16 -
6 C 0 HBD1 (30), DMAP (10) 17 66:34 -
7 D 0 HBD1 (30), DMAP (10) 42 73:27 -
8 E 0 HBD1 (30), DMAP (10) 40 74:26 -
9 A 0 HBD1 (30), DMAP (10) 84 92:8 20
10 A 0 HBD1 (30), DMAP (10) 94 91:9 24
11 A 0 HBD1 (30) 81 96:4 36
12 A 0 HBD1 (30), DMAP (5) 85 94:6 24
graphic file with name nihms702042t2.jpg
a

Isolated yields.

b

Determined by HPLC (chiral stationary phase).