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For a review and some recent examples: (a) Silva, L. F., Jr. Tetrahedron 2002, 58, 9137-9161.
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Silva Jr., L.F.1
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(b) Kita, Y.; Higuchi, K.; Yoshida, Y.; Iio, K.; Kitagaki, S.; Uede, K.; Akai, S.; Fujioka, H. J. Am. Chem. Soc. 2001, 123, 3214-3222.
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Kita, Y.1
Higuchi, K.2
Yoshida, Y.3
Iio, K.4
Kitagaki, S.5
Uede, K.6
Akai, S.7
Fujioka, H.8
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3
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0037154773
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(c) Grellepois, F.; Chorki, F.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J. P. J. Org. Chem. 2002, 67, 1253-1260.
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Bonnet-Delpon, D.5
Bégué, J.P.6
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(d) Kita, Y.; Futayama, J.; Ohba, Y.; Sawama, Y.; Ganesh, J. K.; Fujioka, H. J. Org. Chem. 2003, 68, 5917-5924.
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Kita, Y.1
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5
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0001312924
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Patterden, G., Ed., Pergamon: Oxford, Chapter 33
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For a review: Rickborn, B. In Comprehensive Organic Synthesis, Carbon-Carbon σ-Bond Formation; Patterden, G., Ed., Pergamon: Oxford, 1991; Vol. 3, Chapter 3.3, pp 733-775.
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Rickborn, B.1
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4: Sudha, R.; Narashimhan, K. M.; Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1996, 61, 1877-1879.
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Sankararaman, S.4
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9
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4: Anderson, A. M.; Blazek, J. M.; Garg, P.; Payne, B. J.; Mohan, R. S. Tetrahedron Lett. 2000, 41, 1527-1530.
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Anderson, A.M.1
Blazek, J.M.2
Garg, P.3
Payne, B.J.4
Mohan, R.S.5
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3543085338
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note
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5: see ref 4d.
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(a) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431-6432.
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(b) Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983-6998.
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(c) Maruoka, K.; Ooi, T.; Yamamoto, H. Tetrahedron 1992, 48, 3303-3312.
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(d) Maruoka, K.; Murase, N.; Bureau, R.; Ooi, T.; Yamamoto, H. Tetrahedron 1994, 50, 3663-3672.
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Yamamoto, H., Ed., Oxford: New York; Chapter 2
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(e) Maruoka, K. In Lewis Acid Reagents; Yamamoto, H., Ed., Oxford: New York, 1999; Chapter 2, pp 5-29.
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Maruoka, K.1
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0029951958
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Applications of MABR-mediated rearrangement of epoxides to natural product synthesis: (a) Bando, T.; Shishido, K. Chem. Commun. 1996, 1357-1358.
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Bando, T.1
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0032575171
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(b) Matsushita, M.; Maeda, H.; Kodama, M. Tetrahedron Lett. 1998, 39, 3749-3752.
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Matsushita, M.1
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19
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0037162670
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(c) Kimura, T.; Yamamoto, N.; Suzuki, Y.; Kawano, K.; Norimine, Y.; Ito, K.; Nagato, S.; Iimura, Y.; Yonaga, M. J. Org. Chem. 2002, 67, 6228-6231.
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Yonaga, M.9
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20
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3543107571
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note
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This requirement sometimes imposes several practical limitations on this valuable reagent, including the need for special workup techniques (see refs 4b and 4e).
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21
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0000695467
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4, work as useful Lewis acid catalysts for the rearrangement of epoxides to carbonyl compounds: (a) Takanami, T.; Hirabe, R.; Ueno, M.; Hino, F.; Suda, K. Chem. Lett. 1996, 1031-1032.
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Takanami, T.1
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(b) Suda, K.; Baba, K.; Nakajima, S.; Takanami, T. Tetrahedron Lett. 1999, 40, 7243-7246.
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Suda, K.1
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Takanami, T.4
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24
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3543063181
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Several synthetically useful metalloporphyrin-catalyzed reactions have recently been reported: (a) Chen, Y.; Huang, L.; Zhang, X. P. Org. Lett. 2003, 2493-2496.
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Org. Lett.
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Chen, Y.1
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0037008610
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Oshima et al. reported a related rearrangement of 2,3-epoxy alcohols induced by gem-dizinc reagents: Matsubara, S.; Yamamoto, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 2837-2840.
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Matsubara, S.1
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Oshima, K.3
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0000194931
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3-mediated stereoselective rearrangements of epoxides: (a) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208-12209.
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Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898.
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3543078386
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note
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Kimura et al. have reported that MAD, methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide, can induce the rearrangement of epoxide 1g to aldehyde 3g (see ref 5c).
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