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For a selection of recent reports of carbonyl-ene and related cyclizations in stereoselective syntheses of biologically active molecules, see: a B. Alcaide, C. Pardo, C. Rodriguez-Ranera, A. Rodriquez-Vicente, Org. Lett. 2001, 3, 4205-4208;
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For a selection of recent reports of carbonyl-ene and related cyclizations in stereoselective syntheses of biologically active molecules, see: a) B. Alcaide, C. Pardo, C. Rodriguez-Ranera, A. Rodriquez-Vicente, Org. Lett. 2001, 3, 4205-4208;
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c) K. Mikami, S. Ohba, H. Ohmura, N. Kubodera, K. Nakagawa, T. Okano, Chirality 2001, 13, 366-371;
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5
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0001230709
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For reviews of the ene reaction, including the carbonyl-ene reaction and cyclization, see: a
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For reviews of the ene reaction, including the carbonyl-ene reaction and cyclization, see: a) H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597-618;
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Carruthers, W.1
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For a review of advances in enantioselective catalytic ene reactions, see: a, Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, chap. 32.3;
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For a review of advances in enantioselective catalytic ene reactions, see: a) K. Mikami, M. Terrada in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, chap. 32.3;
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Mikami, K.1
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0001226063
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For examples of enantioselective intermolecular carbonyl-ene reactions of electron-deficient aldehydes, such as chloral and fluoral, see: a K. Maruoka, Y. Hoshino, T. Shirasaka, H. Yamamoto, Tetrahedron Lett. 1988, 29, 3967-3970;
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For examples of enantioselective intermolecular carbonyl-ene reactions of electron-deficient aldehydes, such as chloral and fluoral, see: a) K. Maruoka, Y. Hoshino, T. Shirasaka, H. Yamamoto, Tetrahedron Lett. 1988, 29, 3967-3970;
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b) K. Mikami, T. Yajima, T. Takasaki, S. Matsukawa, M. Terada, T. Uchimaru, M. Maruta, Tetrahedron 1996, 52, 85-98.
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15
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For examples of enantioselective intermolecular carbonyl-ene reactions of glyoxalate and pyruvate derivatives, see: a K. Aikawa, S. Kainuma, M. Hatano, K. Mikami, Tetrahedron Lett. 2004, 45, 183-185;
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For examples of enantioselective intermolecular carbonyl-ene reactions of glyoxalate and pyruvate derivatives, see: a) K. Aikawa, S. Kainuma, M. Hatano, K. Mikami, Tetrahedron Lett. 2004, 45, 183-185;
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b) K. Mikami, M. Terada, T. Nakai, J. Am. Chem. Soc. 1989, 111, 1940-1941;
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c) K. Mikami, M. Terada, T. Nakai, J. Am. Chem. Soc. 1990, 112, 3949-3954;
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e) S. Pandiaraju, G. Chen, A. Lough, A. K. Yudin, J. Am. Chem. Soc. 2001, 123, 3850-3851;
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g) S. Kezuka, T. Ikeno, T. Yamada, Org. Lett. 2001, 3, 1937-1939;
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j) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky, S. W. Tregay, J. Am. Chem. Soc. 1998, 120, 5824-5825;
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k) D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras, T. Vojkovsky, J. Am. Chem. Soc. 2000, 122, 7936-7943;
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For examples of enantioselective catalytic intermolecular carbonyl-ene reactions of unactivated aldehydes see: a E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650;
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For examples of enantioselective catalytic intermolecular carbonyl-ene reactions of unactivated aldehydes see: a) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650;
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31
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0000995013
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For enantioselective carbonyl-ene cyclizations promoted by a more than stoichiometric amount of Zn/binol system, see: S. Sakane, K. Maruoka, H. Yamamoto, Tetrahedron 1986, 42, 2203-2209
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For enantioselective carbonyl-ene cyclizations promoted by a more than stoichiometric amount of Zn/binol system, see: S. Sakane, K. Maruoka, H. Yamamoto, Tetrahedron 1986, 42, 2203-2209.
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32
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0026344849
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For enantioselective catalysis of carbonyl-ene cyclizations by Ti complexes, see: a
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For enantioselective catalysis of carbonyl-ene cyclizations by Ti complexes, see: a) K. Mikami, E. Sawa, M. Terada, Tetrahedron: Asymmetry 1991, 2, 1403-1412;
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Tetrahedron: Asymmetry
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b) K. Mikami, Y. Koizumi, A. Osawa, M. Terada, H. Takayama, K. Nakagawa, T. Okano, Synlett 1999, 11, 1899-1902.
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34
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II-catalyzed enantioselective cyclizations of α-keto esters, see: D. Yang, M. Yang, N. Zhu, Org. Lett. 2003, 5, 3749-3752.
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II-catalyzed enantioselective cyclizations of α-keto esters, see: D. Yang, M. Yang, N. Zhu, Org. Lett. 2003, 5, 3749-3752.
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35
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0025330437
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The desymmetrization of dialdehydes by ene cyclization has been investigated by Ziegler and Sobolov in an approach to the synthesis of the natural product anguidine: F. E. Ziegler, S. B. Sobolov, J. Am. Chem. Soc. 1990, 112, 2749-2758
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The desymmetrization of dialdehydes by ene cyclization has been investigated by Ziegler and Sobolov in an approach to the synthesis of the natural product anguidine: F. E. Ziegler, S. B. Sobolov, J. Am. Chem. Soc. 1990, 112, 2749-2758.
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Intramolecular reactions of these substrates presumably also benefit from a Thorpe-Ingold effect. For a recent review, see
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Intramolecular reactions of these substrates presumably also benefit from a Thorpe-Ingold effect. For a recent review, see: M. E. Jung, G. Piizi, Chem. Rev. 2005, 105, 1735-1766.
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Chem. Rev
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33646403425
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For a recent review of approaches to tetrahydropyran frameworks, see
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For a recent review of approaches to tetrahydropyran frameworks, see: P. A. Clarke, S. Santos, Eur. J. Org. Chem. 2006, 2045-2053.
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Eur. J. Org. Chem
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Clarke, P.A.1
Santos, S.2
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38
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See the Supporting Information for X-ray crystallographic data
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See the Supporting Information for X-ray crystallographic data.
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39
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53549131210
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See the Supporting Information for substrate preparation
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See the Supporting Information for substrate preparation.
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