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J. Yu, M. Lu
LETTER
(5) Hartmann, R. W.; Hector, M.; Haidar, S.; Ehmer, P. B.;
isolated yields of the products after purification by silica-gel col-
umn chromatography (300 mesh).
Reichert, W.; Jose, J. J. Med. Chem. 2000, 43, 4266.
6) Mendelsohn, B. A.; Lee, S.; Kim, S.; Teyssier, F.; Aulakh,
V. S.; Ciufolini, M. A. Org. Lett. 2009, 11, 1539.
(
(
(
Typical Procedure for the Aerobic Oxidative Synthesis of
Oximes
7) Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett.
THICA was prepared by the literature procedure (Scheme 3).18 1H
2
007, 9, 3599.
1
3
NMR (500 MHz, DMSO-d ): δ = 11.177 (s, 3 H) ppm. C NMR
6
8) (a) Shono, T.; Matsumura, Y.; Tsubata, K.; Kamada, T.;
Kishi, K. J. Org. Chem. 1989, 54, 2249. (b) Yang, S. H.;
Chang, S. Org. Lett. 2001, 3, 4209. (c) Yamaguchi, K.;
Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N.
Angew. Chem. Int. Ed. 2007, 46, 3922. (d) Owston, N. A.;
Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 3599.
(
2
125 MHz, DMSO-d ): δ = 149.923 ppm. IR: 3400, 3080,
830,1710, 1510, 1420, 1390, 1240, 968, 713 cm .
6
–
1
A mixture of primary amine (1 mmol), THICA (5 mol%), acetal-
doxime (10 mol%), and H O (5 mL) was placed in a three-necked
flask. O was stirred into the flask at a flow rate of 20 mL/min. The
reaction mixture was stirred at 100 °C for several hours, and the re-
action progress was monitored by TLC. When the final reaction
mixture was cooled to r.t. and extracted with Et O, the organic layer
was washed with brine, dried over MgSO , and concentrated under
reduced pressure. The residue was pure enough. When necessary,
the crude product was purified by chromatography using EtOAc–
PE (1:8) as eluent.
2
2
(e) Fujiwara, H.; Ogasawara, Y.; Yamaguchi, K.; Mizuno,
N. Angew. Chem. Int. Ed. 2007, 46, 5202.
2
(9) Pohjakallio, A.; Pihko, P. M. Chem. Eur. J. 2009, 15, 3960.
4
(
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1
(
4
6
Supporting Information for this article is available online
at
(
1
10.1055/s-00000083.SunpfgIpi
o
nr
i
o
Soc. 1939, 61, 3194.
(
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