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compounds. This material is available free of charge via the
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’ AUTHOR INFORMATION
(11) A versatile organocatalytic aerobic oxidation method was
reported recently using 5-Fluoro-2-azaadamantane-N-oxyl (F-AZADO)
or the corresponding oxammonium nitrate salt as the catalyst. These
reactions exhibit broad scope, including 1° and 2° allylic, benzylic and
aliphatic substrates. The reactions were performed with an air balloon in
acetic acid as the solvent. This catalyst is not yet available commercially,
however the parent AZADO species can be obtained from Aldrich
(250 mg, $219). For leading references, see: (a) Shibuya, M.; Osada, Y.;
Sasano, Y.; Tomizawa, M.; Iwabuchi, Y. J. Am. Chem. Soc. 2011,
133, 6497–6500. (b) Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi,
Y. J. Am. Chem. Soc. 2006, 128, 8412–8413.
Corresponding Author
’ ACKNOWLEDGMENT
We are grateful to Charles Alt (Eli Lilly) for performing
HPLC analysis of the aldehyde product in Table 4, entry 5.
Financial support of this work was provided by the NIH (RC1-
GM091161), the ACS GCI Pharmaceutical Roundtable and the
Camille and Henry Dreyfus Postdoctoral Program in Environ-
mental Chemistry. NMR spectroscopy facilities were partially
supported bytheNSF (CHE-9208463) and NIH(S10 RR08389).
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