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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 2.

Catalyst Loading Comparison Of Two Catalystsa

graphic file with name nihms532320u3.jpg
PBAM (17) 6,8 (MeO)2PBAM (23)
entry mol% ee (%)b yield (%)c entry mol% ee (%)b yield (%)c
1 20 53 39 1 15.4 62 58
2 10 65 59 2 7.7 73 68
3 5 70 71 3 3.9 79 75
4 2 73 76 4 1.5 84 74
5 1 74 76 5 0.77 86 79
6d 1 80 78 6 0.38 87 79
7 0.15 87 73
a

0.1 mmol scale, 1.1 equiv. of 8, 0.1 M in toluene, 18–24 h reaction time.

b

Determined by chiral HPLC.

c

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

d

0.2 equiv imine added, 30 min intervals.