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. Author manuscript; available in PMC: 2014 Nov 1.
Published in final edited form as: J Org Chem. 2013 Oct 15;78(21):10.1021/jo401321a. doi: 10.1021/jo401321a

Table 3.

Aryl Nitromethane Addition Scale-up/Optimization

graphic file with name nihms532320u4.jpg
entry mol% mmol conc. (M) ee (%)a yield (%)b
1 2 0.4 0.1 91 82
2 1 0.4 0.1 92 78
3 1 0.4 0.2 92 84
4 1 0.4 0.4 91 84
5 0.5 0.4 0.4 91 81
6c 0.5 2 0.4 77–94 81–90
7d 0.5 2 0.4 86 86
8e 0.5 20 0.4 89 90
9e 0.5 25 0.4 89 89
a

Enantiomer ratios of isolated material measured by HPLC using chiral stationary phases.

b

Isolated yield of single diastereomer (200:1 dr by HPLC) after filtration/washing.

c

Results of 4 runs.

d

Imine added in 0.2 equiv increments.

e

Imine added in 0.1 equiv increments.