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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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Kido, M.5
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0345411573
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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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Ishibashi, H.1
Nakamura, N.2
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Takeuchi, M.4
Ikeda, M.5
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19
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0026519516
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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993-1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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Piva, O.3
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0026710414
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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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Ukaji, Y.2
Noro, T.3
Date, K.4
Shimizu, M.5
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21
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0000038142
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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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Miyamoto, H.2
Takeda, K.3
Matsugawa, R.4
Maruyama, N.5
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0029798970
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Synthesis of spiro-fused azetidinone: (a) Wittig, G.; Hesse, A. Liebigs Ann. Chem. 1976, 500-510. (b) Spurr, P. R.; Hamon, D. P. G. J. Am. Chem. Soc. 1983, 105, 4734-4739. (c) Ikeda, M.; Uchino, T.; Ishibashi, H.; Tamura, Y.; Kido, M. J. Chem. Soc., Chem. Commun. 1984, 758-759. (d) Mullen, G. B.; Georgiev, V. S. Heterocycles 1986, 24, 3441-3446. (e) Ishibashi, H.; Nakamura, N.; Tatsunori, S.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. (f) Le Blanc, S.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 1993- 1996. (g) Fujisawa, T.; Ukaji, Y.; Noro, T.; Date, K.; Shimizu, M. Tetrahedron 1992, 48, 5629-5638. (h) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208-6211. (i) Chen, L.; Zaks, A.; Chacklamanil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343.
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After submission of our paper, a diastereo- and enantioselective synthesis of cholesterol absorption inhibitors has been reported. Wu, G.; Wong, Y.; Chen, X.; Ding, Z. J. Org. Chem. 1999, 64, 3714-3718.
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(a) Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. Chem. Commun. 1999, 715-716.
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Kambara, T.5
Nomura, Y.6
Kanai, M.7
Koga, K.8
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30
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0344117742
-
-
The absolute configuration of 6 has not yet been determined
-
The absolute configuration of 6 has not yet been determined.
-
-
-
-
31
-
-
0344117743
-
-
Use of LDA did not exceed the selectivity obtained by use of LICA
-
Use of LDA did not exceed the selectivity obtained by use of LICA.
-
-
-
-
32
-
-
0344980313
-
-
The ternary complex of 10 did not afford satisfactory selectivity
-
The ternary complex of 10 did not afford satisfactory selectivity.
-
-
-
-
33
-
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0344117741
-
-
Purification was carried out using silica gel column chromatography unless otherwise noted
-
Purification was carried out using silica gel column chromatography unless otherwise noted.
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-
-
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34
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0345411570
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(a) Hardegger, E.; Plattner, P. A.; Blank, F. Helv. Chim. Acta 1944, 27, 793-800.
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