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O
OH
HO
O
O
heat
4. (a) Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55,
3715–3717; (b) Schwarz, J. B.; Meyers, A. I. J. Org. Chem.
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Lefker, B. A.; Hada, W. A.; McGarry, P. J. Tetrahedron
Lett. 1994, 35, 5205–5208; (e) Hashiyama, T.; Morikawa,
K.; Sharpless, B. K. J. Org. Chem. 1992, 57, 5067–5068; (f)
Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron
O
+
O
Scheme 3. Enolization and dimerization of a-hydroxy ketones.
ketones and it appears that this process is an oxidation
pathwayrather than enolization or dimerization. It does
result in loss of optical activity.
ꢀ
Lett. 1997, 38, 5051–5054; (g) Solladie-Cavallo, A.;
Lupattelli, P.; Jierry, L.; Bovicelli, P.; Angeli, F.; Anto-
nioletti, R.; Klein, A. Tetrahedron Lett. 2003, 44, 6523–
6526.
In summary, we have established that the asymmetric
dihydroxylation of allenes is a suitable method for
enantioselective formation of the a-hydroxy ketones.
We are continuing to explore the scope of this meth-
odologyparticularlywith respect to the chemistryof
disubstituted allenes.
5. (a) Fukuzawa, S.; Miura, M.; Matsuzawa, H. Tetrahedron
Lett. 2001, 42, 4167–4169; (b) Yu, H.; Ballard, E.; Wang,
B. Tetrahedron Lett. 2001, 42, 1835–1838.
6. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B.
Chem. Rev. 1994, 94, 2483–2547; See also: Corey, E. J.;
Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861–
2864.
7. Claesson, A.; Olsson, L.-I. J. Am. Chem. Soc. 1979, 101,
7302–7311.
Supplementary material Supplementarydata including
1H NMR, 13C NMR, and HRMS is available online
with the paper in ScienceDirect.
8. Literature reference for phenylallene: Ma, S.; Zhang, A.
J. Org. Chem. 1998, 63, 9601–9604; Literature reference
for 4-methylphenylallene and 4-chlorophenylallene: Oku-
yama, T.; Izawa, K.; Fueno, T. J. Am. Chem. Soc. 1973,
95, 6749–6752; Literature reference with partial NMR
data for 4-methoxyphenylallene: Koole, N. J.; Bie, M. J.
A. Org. Magn. Reson. 1984, 22, 146–163; Literature
reference for 2-methylphenylallene: Huang, C.-W.; Shan-
mugasundaram, M.; Chang, H.-M.; Cheng, C.-H. Tetra-
hedron 2003, 49, 3635–3641; Literature reference for
2-naphthylallene with incomplete data: Satoh, T.; Kuramo-
chi, Y.; Inoue, Y. Tetrahedron Lett. 1999, 40, 8815–8818.
9. (a) Literature reference for 1-hydroxy-1-phenylpropanone:
see Ref. 4c (b) Literature reference for 1-hydroxy-1-(4-
Acknowledgements
We thank the Department of Chemistryand Biochem-
istryat Brigham Young Universityand the Talmage
Summer Internship for support (J.H. and S.M.C.).
References and notes
€
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each hydroxy ketone. Racemic material was obtained by
standard OsO4/NMO oxidation of the corresponding
allenes.
ꢀ
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