C O M M U N I C A T I O N S
162. (d) Gonza´lez-Nu´n˜ez, M. E.; Royo, J.; Mello, R.; Ba´guena, M.; Ferrer,
J. M.; Ram´ırez de Arellano, C.; Asensio, G.; Prakash, G. K. S. J. Org.
Chem. 2005, 70, 7919-7924.
represent a significant step toward the development of general
methodology for the catalytic hydroxylation of C-H bonds.
(11) Calculations performed using: Frisch, M. J. et al. Gaussian 03, revision
C.02; Gaussian, Inc.: Wallingford, CT, 2004.
Acknowledgment. The authors wish to thank Xavier Otten-
waelder for X-ray crystallographic analysis, and Professor Charles
Musgrave for helpful discussions. B.H.B. has been supported by
an Eli Lilly Graduate Fellowship. We are grateful to the Beckman
Foundation, the A. P. Sloan Foundation, the Camille and Henry
Dreyfus Foundation, the Arthur C. Cope Fund, and to Abbott
Laboratories, Amgen, Boehringer Ingelheim, Bristol-Myers Squibb,
Eli Lilly, GlaxoSmithKline, Merck, Pfizer, and Roche for financial
support.
(12) Activation energies were calculated relative to isolated reactants.
(13) For representative examples, see: (a) Wender, P. A.; Hilinski, M. K.;
Mayweg, A. V. W. Org. Lett. 2005, 7, 79-82. (b) Horiguchi, T.; Cheng,
Q.; Oritani, T. Tetrahedron Lett. 2000, 41, 3907-3910. (c) Bovicelli, P.;
Lupattelli, P.; Mincione, E.; Prencipe, T.; Curci, R. J. Org. Chem. 1992,
57, 2182-2184.
(14) For previous computational work on oxaziridines, see: (a) Houk, K. N.;
Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119,
10147-10152. (b) Bach, R. D.; Andre´s, J. L.; Davis, F. A. J. Org. Chem.
1992, 57, 613-618.
(15) (a) Bach, R. D.; Dmitrenko, O.; Adam, W.; Schambony, S. J. Am. Chem.
Soc. 2003, 125, 924-934. (b) Bach, R. D.; Glukhovtsev, M. N.; Gonzalez,
C.; Marquez, M.; Este´vez, C. M.; Baboul, A. G.; Schlegel, H. B. J. Phys.
Chem. A 1997, 101, 6092-6100.
Supporting Information Available: A complete list of authors for
ref 11 can be found in ref 2, page S9. Experimental details, X-ray
crystallographic, and analytical data for all compounds are available.
This material is available free of charge via the Internet at http://
pubs.acs.org.
(16) Glukhovtsev, M. N.; Canepa, C.; Bach, R. D. J. Am. Chem. Soc. 1998,
120, 10528-10533.
1
(17) A comparative table of selected bond lengths and angles for TSM and
DMDO
TSM
is included in the Supporting Information.
(18) The restricted B3LYP wave function exhibits an RHF f UHF instability
similar to that observed for TSMDMDO. Calculations using the stable
1
unrestricted B3LYP wave function on TSM led to a decrease in energy
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