2582
B. Puget, U. Jahn
LETTER
(5) In a single example of a ortho metalation, but after a-
Supporting Information for this article is available online at
deprotonation, the resulting dianion rearranges under harsh
conditions: (a) Vollhardt, J.; Gais, H.-J.; Lukas, K. L.
Angew. Chem., Int. Ed. Engl. 1985, 24, 610. Application:
(b) Gais, H.-J.; Ball, W. A.; Bund, J. Tetrahedron Lett. 1988,
29, 781.
Acknowledgment
We gratefully acknowledge generous funding by a grant of the Aca-
demy of Sciences of the Czech Republic (Z4 055 0506).
(6) (a) Pospíšil, J.; Pospíšil, T.; Markó, I. E. Org. Lett. 2005, 7,
2373. (b) Markó, I. E.; Murphy, F.; Dolan, S. Tetrahedron
Lett. 1996, 37, 2089.
(7) For a recent application, see: Yang, D.; Micalizio, G. C.
J. Am. Chem. Soc. 2009, 131, 17548.
References
(8) Recent reviews: (a) Le Marquand, P.; Tam, W. Angew.
Chem. Int. Ed. 2008, 47, 2926. (b) Chan, D. M. T. In
Cycloaddition Reactions in Organic Synthesis; Kobayashi,
S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002,
57. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523. (d) Trost,
B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
(9) Recent reviews: (a) Smith, A. B. III.; Wuest, W. M. Chem.
Commun. 2008, 5883. (b) Schaumann, E.; Kirschning, A.
Synlett 2007, 177. (c) Moser, W. H. Tetrahedron 2001, 57,
2065. (d) Brook, A. G.; Bassendale, A. R. In
(1) (a) Reviews: Aïssa, C. Eur. J. Org. Chem. 2009, 1831.
(b) El-Awa, A.; Noshi, M. N.; Mollat, X. J.; Fuchs, P. L.
Chem. Rev. 2009, 109, 2315. (c) Dumeunier, R.; Markó,
I. E. In Modern Carbonyl Olefination; Takeda, T., Ed.;
Wiley-VCH: Weinheim, 2004, 104. (d) Blakemore, P. R.
J. Chem. Soc., Perkin Trans. 1 2002, 2563. (e) Kociensky,
P. J. In Comprehensive Organic Synthesis, Vol. 6; Trost,
B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 987.
(2) Jahn, U.; Hartmann, P.; Kaasalainen, E. Org. Lett. 2004, 6,
257.
Rearrangements in Ground and Excited States, Vol. 2;
de Mayo, P., Ed.; Academic Press: New York, 1980, 149.
(10) ortho-Deprotonation is also observed for 8, but only after
a-deprotonation: (a) Cabiddu, S.; Fattuoni, C.; Floris, C.;
Gelli, G.; Melis, S. Synthesis 1993, 41. (b) Cabiddu, M.;
Cabiddu, S.; Fattuoni, C.; Floris, C.; Gelli, G.; Melis, S.
Phosphorus, Sulfur Silicon Relat. Elem. 1992, 70, 139.
(11) Engel, W.; Fleming, I.; Smithers, R. H. J. Chem. Soc., Perkin
Trans. 1 1986, 1637.
(3) For other methods, see: (a) Uenishi, J.; Iwamoto, T.; Ohmi,
M. Tetrahedron Lett. 2007, 48, 1237. (b) Uenishi, J.; Ohmi,
M. Angew. Chem. Int. Ed. 2005, 44, 2756. (c) Kercher, T.;
Livinghouse, T. J. Org. Chem. 1997, 62, 805. (d) Kercher,
T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200.
(e) Wang, K. K.; Dhumrongvaraporn, S. Tetrahedron Lett.
1987, 28, 1007.
(4) (a) Iwao, M.; Iihama, T.; Mahalanabis, K. K.; Perrier, H.;
Snieckus, V. J. Org. Chem. 1989, 54, 24. (b) MacNeil, S.
L.; Familoni, O. B.; Snieckus, V. J. Org. Chem. 2001, 66,
3662.
Synlett 2010, No. 17, 2579–2582 © Thieme Stuttgart · New York