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. 2014 Oct 30;79(23):11631–11643. doi: 10.1021/jo502288q

Table 1. Effect of Temperature, Oxygen, and Scale.

graphic file with name jo-2014-02288q_0013.jpg

entry T (°C) t (h) yield of 2a yield of 1a exo:endo ratioa
1 22 16 57 <5 5.5:1
2 5 8 53 <5 5.1:1
3b 22 16 24 42 4.3:1
4c 5 12.5 6 80 3.3:1
5d 5 12.5 22 44 2.7:1
6e 5 12.5 33 29 4.6:1
7f 5 13 40 26 3.5:1
8g 5 13 40 23 3.3:1
a

Calculated by UPLC (PDA).

b

Reaction performed at a 0.50 mmol scale.

c

Reaction deoxygenated via freeze–pump–thaw.

d

Reaction performed under a balloon of oxygen.

e

Reaction performed under a balloon of air.

f

Reaction sparged continuously with air (0.25 mmol scale).

g

Reaction sparged continuously with air (0.50 mmol scale).