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. Author manuscript; available in PMC: 2013 Jun 19.
Published in final edited form as: Adv Synth Catal. 2008 Jul 24;350(11-12):1785–1790. doi: 10.1002/adsc.200800214

Table 1.

Screen of thioureas catalysts with Boc imine 14a.a

graphic file with name nihms442486u1.jpg
entry catalyst Et3N (equiv) % conversion b % ee c
1 (1S,2S)-1 0.4 100 8
2 (R)-5 0
3 (R)-5 0.4 50 4
4 (R)-6 65 5
5 (R)-7 0.4 100 5
6 (R)-8 0.4 10 4
7 (R)-9 0.4 36 0
8 (R)-10 0.4 100 16
9 (R)-11 0.4 73 <5
10 (R)-12 0.4 100 74
11 (R,R)-13 0.4 100 6
a

Reactions conducted with 10 equiv CH3NO2 and 20 mol % catalyst in toluene at 25 °C for 12 h except entry 10 which was 2 h.

b

Determined by 1H NMR spectrum of crude reaction mixture.

c

Determined by HPLC on Chiralpak OJ-H column.