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. Author manuscript; available in PMC: 2013 Sep 5.
Published in final edited form as: J Am Chem Soc. 2012 Aug 23;134(35):14334–14337. doi: 10.1021/ja306771n

Table 2.

Reaction optimizationa

graphic file with name nihms402714u2.jpg
Entry cat. T(°C) t(h) conv. (%)b ee (%)b
1 DHQ-3 rt 0.5 47 5
2 DHQ-3 rt 0.5 16 0
3 Q-5 rt 0.5 38 8
4 Q-6 rt 0.5 < 5 -
5 DHQ-7a rt 0.5 97 26
6 DHQ-7b rt 0.5 80 17
7 DHQ-7c rt 0.5 71 31
8 DHQ-7d rt 0.5 62 38
9 DHQ-7e rt 0.5 90 58
c10 DHQ-7f rt 0.5 95 68
11 DHQ-7g rt 0.5 98 28
12 DHQ-7f -20 12 87 78
d13 DHQ-7f -20 72 80 82
e14 DHQ-7f -20 24 71 88
f15 DHQ-7f -20 24 84 88
f16 DHQ-7f -30 48 81 90
a

Unless specified, the reaction was carried out with 1Da (0.05 mmol) in CH2Cl2 (0.05 mL) in the presence of catalyst (0.005 mmol).

b

Determined by HPLC analysis.

c

After 48h, the ee value was reduced to 46%.

d

The reaction was performed in CH2Cl2 (0.50 mL).

e

The reaction was performed in PhMe (0.50 mL).

f

The reaction was performed with 1Da (0.05 mmol) and 4 Ǻ MS (5.0 mg) in PhMe (0.50 mL) in the presence of DHQ-7f (0.005 mmol).