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. Author manuscript; available in PMC: 2014 Jan 18.
Published in final edited form as: J Org Chem. 2012 Dec 28;78(2):506–515. doi: 10.1021/jo3023632

Table 4.

Scaling-up of the catalytic aminooxygenation reaction of aliphatic substrates

graphic file with name nihms-430991-t0021.jpg

entry substrate amount substrate
(mg, mmol)		 yield (%)a ee (%)b
1c 6a, R = Ts 50, 0.19 97 88
1c 6a, R = Ts 250, 0.93 19d 85
2e 6a, R = Ts 250, 0.93 88f 86
3 6a, R = Ts 250, 0.93 95 90
4 6c, R = 3,5-di-t-Bu-4-
MeOC6H2SO2 		300, 0.76 89 95
5 6c, R =3,5-di-t-Bu-4-
MeOC6H2SO2 		1000, 2.53 88 97
a

Yield (%) refers to amount of isolated 7 after purification by flash chromatography on SiO2.

b

Enantiomeric excesses were determined by chiral HPLC analysis.

c

The reaction was run at 120 °C using 3 equiv of TEMPO.

d

80% of the starting alkene 6a was recovered.

e

The reaction was run at 110 °C using 3 equiv of TEMPO.

f

9% of the starting alkene 6a was recovered.