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Volumn 2, Issue 7, 2004, Pages 1077-1085

Direct catalytic asymmetric aldol reactions of pyruvates: Scope and mechanism

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARBON; CATALYSIS; ENZYMES; ETHERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 2342646154     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b316092k     Document Type: Article
Times cited : (74)

References (120)
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    • For Lewis acid catalyzed reactions see e.g.: Sn(II) (a) S. Kobayashi, H. Uchiro, Y. Fijishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; (b) D. A. Evans, D. W. C. MacMillan and K. R. Campos, J. Am. Chem. Soc., 1997, 119, 10859; (c) B(III) K. Furuta, Y. Miwa, K. Iwanaga and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 6254; (d) K. Furuta, T. Maruyama and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 1041; (e) E. R. Parmee, O. Tempkin and S. Masamune, J. Am. Chem. Soc., 1991, 113, 9365; (f) E. J. Corey, C. L. Cywin and T. D. Rober, Tetrahedron Lett., 1992, 33, 6907; (g) Ti(IV) K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 1993, 115, 7039; (h) Cu(II) see ref. 4c.f.
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    • Kobayashi, S.1    Uchiro, H.2    Fijishita, Y.3    Shiina, I.4    Mukaiyama, T.5
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  • 12
    • 0000224603 scopus 로고
    • For Lewis acid catalyzed reactions see e.g.: Sn(II) (a) S. Kobayashi, H. Uchiro, Y. Fijishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; (b) D. A. Evans, D. W. C. MacMillan and K. R. Campos, J. Am. Chem. Soc., 1997, 119, 10859; (c) B(III) K. Furuta, Y. Miwa, K. Iwanaga and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 6254; (d) K. Furuta, T. Maruyama and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 1041; (e) E. R. Parmee, O. Tempkin and S. Masamune, J. Am. Chem. Soc., 1991, 113, 9365; (f) E. J. Corey, C. L. Cywin and T. D. Rober, Tetrahedron Lett., 1992, 33, 6907; (g) Ti(IV) K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 1993, 115, 7039; (h) Cu(II) see ref. 4c.f.
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    • 0001015876 scopus 로고
    • For Lewis acid catalyzed reactions see e.g.: Sn(II) (a) S. Kobayashi, H. Uchiro, Y. Fijishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; (b) D. A. Evans, D. W. C. MacMillan and K. R. Campos, J. Am. Chem. Soc., 1997, 119, 10859; (c) B(III) K. Furuta, Y. Miwa, K. Iwanaga and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 6254; (d) K. Furuta, T. Maruyama and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 1041; (e) E. R. Parmee, O. Tempkin and S. Masamune, J. Am. Chem. Soc., 1991, 113, 9365; (f) E. J. Corey, C. L. Cywin and T. D. Rober, Tetrahedron Lett., 1992, 33, 6907; (g) Ti(IV) K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 1993, 115, 7039; (h) Cu(II) see ref. 4c.f.
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    • 0026452032 scopus 로고
    • For Lewis acid catalyzed reactions see e.g.: Sn(II) (a) S. Kobayashi, H. Uchiro, Y. Fijishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; (b) D. A. Evans, D. W. C. MacMillan and K. R. Campos, J. Am. Chem. Soc., 1997, 119, 10859; (c) B(III) K. Furuta, Y. Miwa, K. Iwanaga and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 6254; (d) K. Furuta, T. Maruyama and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 1041; (e) E. R. Parmee, O. Tempkin and S. Masamune, J. Am. Chem. Soc., 1991, 113, 9365; (f) E. J. Corey, C. L. Cywin and T. D. Rober, Tetrahedron Lett., 1992, 33, 6907; (g) Ti(IV) K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 1993, 115, 7039; (h) Cu(II) see ref. 4c.f.
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    • For Lewis acid catalyzed reactions see e.g.: Sn(II) (a) S. Kobayashi, H. Uchiro, Y. Fijishita, I. Shiina and T. Mukaiyama, J. Am. Chem. Soc., 1991, 113, 4247; (b) D. A. Evans, D. W. C. MacMillan and K. R. Campos, J. Am. Chem. Soc., 1997, 119, 10859; (c) B(III) K. Furuta, Y. Miwa, K. Iwanaga and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 6254; (d) K. Furuta, T. Maruyama and H. Yamamoto, J. Am. Chem. Soc., 1991, 113, 1041; (e) E. R. Parmee, O. Tempkin and S. Masamune, J. Am. Chem. Soc., 1991, 113, 9365; (f) E. J. Corey, C. L. Cywin and T. D. Rober, Tetrahedron Lett., 1992, 33, 6907; (g) Ti(IV) K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 1993, 115, 7039; (h) Cu(II) see ref. 4c.f.
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    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5260
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    • List, B.1    Lerner, R.A.2    Barbas III, C.F.3
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    • The pyruvate-dependent aldolase enzyme catalysing this reaction in nature is 4-hydroxy-2-oxo-4-methylglutarate aldolase (EC 4.1.3.17), see ref. 2
    • The pyruvate-dependent aldolase enzyme catalysing this reaction in nature is 4-hydroxy-2-oxo-4-methylglutarate aldolase (EC 4.1.3.17), see ref. 2.
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    • Enders, D.1    Dyker, H.2    Leusink, F.R.3
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    • See e.g.: (a) D. Enders, H. Dyker and F. R. Leusink, Chem. Eur. J., 1998, 4, 311; (b) I. Blank, J. Lin, R. Fumeaux, D. H. Welti and L. B. Fay, J. Agric. Chem., 1996, 44, 1851; (c) J. Bigorra, J. Font, C. Ochoa de Echaguen and R. M. Ortune, Tetrahedron, 1993, 49, 6717; (d) E. Guichard, P. Etivant, R. Henry and A. Mosandl, Z. Lebensm.-Unters.-Forsch., 1992, 195, 540; (e) S. V. Attword and A. G. M. Barret, J. Chem. Soc., Perkin Trans. 1, 1984, 1315; (f) A. G. M. Barret and H. G. Smith, J. Org. Chem., 1983, 48, 5017.
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    • Blank, I.1    Lin, J.2    Fumeaux, R.3    Welti, D.H.4    Fay, L.B.5
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    • Bigorra, J.1    Font, J.2    Ochoa de Echaguen, C.3    Ortune, R.M.4
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    • See e.g.: (a) D. Enders, H. Dyker and F. R. Leusink, Chem. Eur. J., 1998, 4, 311; (b) I. Blank, J. Lin, R. Fumeaux, D. H. Welti and L. B. Fay, J. Agric. Chem., 1996, 44, 1851; (c) J. Bigorra, J. Font, C. Ochoa de Echaguen and R. M. Ortune, Tetrahedron, 1993, 49, 6717; (d) E. Guichard, P. Etivant, R. Henry and A. Mosandl, Z. Lebensm.-Unters.-Forsch., 1992, 195, 540; (e) S. V. Attword and A. G. M. Barret, J. Chem. Soc., Perkin Trans. 1, 1984, 1315; (f) A. G. M. Barret and H. G. Smith, J. Org. Chem., 1983, 48, 5017.
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    • Guichard, E.1    Etivant, P.2    Henry, R.3    Mosandl, A.4
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    • See e.g.: (a) D. Enders, H. Dyker and F. R. Leusink, Chem. Eur. J., 1998, 4, 311; (b) I. Blank, J. Lin, R. Fumeaux, D. H. Welti and L. B. Fay, J. Agric. Chem., 1996, 44, 1851; (c) J. Bigorra, J. Font, C. Ochoa de Echaguen and R. M. Ortune, Tetrahedron, 1993, 49, 6717; (d) E. Guichard, P. Etivant, R. Henry and A. Mosandl, Z. Lebensm.-Unters.-Forsch., 1992, 195, 540; (e) S. V. Attword and A. G. M. Barret, J. Chem. Soc., Perkin Trans. 1, 1984, 1315; (f) A. G. M. Barret and H. G. Smith, J. Org. Chem., 1983, 48, 5017.
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    • Attword, S.V.1    Barret, A.G.M.2
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    • See e.g.: (a) D. Enders, H. Dyker and F. R. Leusink, Chem. Eur. J., 1998, 4, 311; (b) I. Blank, J. Lin, R. Fumeaux, D. H. Welti and L. B. Fay, J. Agric. Chem., 1996, 44, 1851; (c) J. Bigorra, J. Font, C. Ochoa de Echaguen and R. M. Ortune, Tetrahedron, 1993, 49, 6717; (d) E. Guichard, P. Etivant, R. Henry and A. Mosandl, Z. Lebensm.-Unters.-Forsch., 1992, 195, 540; (e) S. V. Attword and A. G. M. Barret, J. Chem. Soc., Perkin Trans. 1, 1984, 1315; (f) A. G. M. Barret and H. G. Smith, J. Org. Chem., 1983, 48, 5017.
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    • Problems isolating unprotected isotetronic acid derivatives have been encountered before; see e.g.: ref. 12a
    • Problems isolating unprotected isotetronic acid derivatives have been encountered before; see e.g.: ref. 12a.
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    • 2-bisoxazoline-Lewis acid catalysts see e.g.: (a) A. K. Ghosh, P. Mathivanen and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1; (b) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain and J. Thorhauge, Acc. Chem. Res., 1999, 32, 605; (c) J. S. Johnson and D. A. Evans, Acc. Chem. Res., 2000, 33, 325.
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    • Ghosh, A.K.1    Mathivanen, P.2    Cappiello, J.3
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    • 2-bisoxazoline-Lewis acid catalysts see e.g.: (a) A. K. Ghosh, P. Mathivanen and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1; (b) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain and J. Thorhauge, Acc. Chem. Res., 1999, 32, 605; (c) J. S. Johnson and D. A. Evans, Acc. Chem. Res., 2000, 33, 325.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 605
    • Jørgensen, K.A.1    Johannsen, M.2    Yao, S.3    Audrain, H.4    Thorhauge, J.5
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    • 2-bisoxazoline-Lewis acid catalysts see e.g.: (a) A. K. Ghosh, P. Mathivanen and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1; (b) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain and J. Thorhauge, Acc. Chem. Res., 1999, 32, 605; (c) J. S. Johnson and D. A. Evans, Acc. Chem. Res., 2000, 33, 325.
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    • Johnson, J.S.1    Evans, D.A.2
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    • and references therein
    • Catalytic enantioselective Diels-Alder reactions, see e.g.: (a) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, R. D. Norcross, E. A. Shaughnessy and K. R. Campos, J. Am. Chem. Soc., 1999, 121, 7582 and references therein; (b) D. A. Evans, S. J. Miller, T. Lectka and P. von Matt, J. Am. Chem. Soc., 1999, 121, 7559 and references therein; (c) V. K. Aggarwal, D. E. Jones and A. M. Martin-Castro, Eur. J. Org. Chem., 2000, 2939.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7582
    • Evans, D.A.1    Barnes, D.M.2    Johnson, J.S.3    Lectka, T.4    Von Matt, P.5    Miller, S.J.6    Norcross, R.D.7    Shaughnessy, E.A.8    Campos, K.R.9
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    • and references therein
    • Catalytic enantioselective Diels-Alder reactions, see e.g.: (a) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, R. D. Norcross, E. A. Shaughnessy and K. R. Campos, J. Am. Chem. Soc., 1999, 121, 7582 and references therein; (b) D. A. Evans, S. J. Miller, T. Lectka and P. von Matt, J. Am. Chem. Soc., 1999, 121, 7559 and references therein; (c) V. K. Aggarwal, D. E. Jones and A. M. Martin-Castro, Eur. J. Org. Chem., 2000, 2939.
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    • Evans, D.A.1    Miller, S.J.2    Lectka, T.3    Von Matt, P.4
  • 63
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    • Catalytic enantioselective Diels-Alder reactions, see e.g.: (a) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, R. D. Norcross, E. A. Shaughnessy and K. R. Campos, J. Am. Chem. Soc., 1999, 121, 7582 and references therein; (b) D. A. Evans, S. J. Miller, T. Lectka and P. von Matt, J. Am. Chem. Soc., 1999, 121, 7559 and references therein; (c) V. K. Aggarwal, D. E. Jones and A. M. Martin-Castro, Eur. J. Org. Chem., 2000, 2939.
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    • Aggarwal, V.K.1    Jones, D.E.2    Martin-Castro, A.M.3
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    • Gothelf, A.S.1    Gothelf, K.V.2    Hazell, R.G.3    Jørgensen, K.A.4
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    • Sibi, M.P.1    Ji, J.2    Wu, J.-H.3    Gurtler, S.4    Porter, N.A.5
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    • Evans, D.A.1    Rovis, T.2    Kozlowski, M.C.3    Tedrow, J.S.4
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    • Hansen, K.B.1    Finney, N.S.2    Jacobsen, E.N.3
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    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (1997) Chem. Commun. , pp. 2169
    • Johannsen, M.1    Yao, S.2    Jørgensen, K.A.3
  • 80
    • 0002428308 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (1998) J. Org. Chem. , vol.63 , pp. 118
    • Yao, S.1    Johannsen, M.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 81
    • 0032475445 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 8599
    • Yao, S.1    Johannsen, M.2    Audrain, H.3    Hazell, R.G.4    Jørgensen, K.A.5
  • 82
    • 0030220901 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2165
    • Ghosh, A.K.1    Mathivanan, P.2    Cappiello, J.3    Krishnan, K.4
  • 83
    • 0032544310 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2404
    • Thorhauge, J.1    Johannsen, M.2    Jørgensen, K.A.3
  • 84
    • 0033521665 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3372
    • Evans, D.A.1    Olhava, E.J.2    Johnson, J.S.3    Janey, J.M.4
  • 85
    • 0034006954 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1635
    • Evans, D.A.1    Johnson, J.S.2    Olhava, E.J.3
  • 86
    • 0034725914 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (2000) J. Org. Chem. , vol.65 , pp. 4487
    • Audrain, H.1    Thorhauge, J.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 87
    • 0034696658 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero-Diels-Alder reactions, see e.g.: (a) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; (b) M. Johannsen and K. A. Jørgensen, Tetrahedron, 1996, 52, 7321; (c) M. Johannsen and K. A. Jørgensen, J. Chem. Soc., Perkin Trans. 2, 1997, 1183; (d) M. Johannsen, S. Yao and K. A. Jørgensen, Chem. Commun., 1997, 2169; (e) S. Yao, M. Johannsen, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 118; (f) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jørgensen, J. Am. Chem. Soc., 1998, 120, 8599; (g) A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165; (h) J. Thorhauge, M. Johannsen and K. A. Jørgensen, Angew. Chem., Int. Ed., 1998, 37, 2404; (i) D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998, 37, 3372; (j) D. A. Evans, J. S. Johnson and E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635; (k) H. Audrain, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2000, 65, 4487; (l) W. Zhuang, J. Thorhauge and K. A. Jørgensen, Chem. Commun., 2000, 459.
    • (2000) Chem. Commun. , pp. 459
    • Zhuang, W.1    Thorhauge, J.2    Jørgensen, K.A.3
  • 88
    • 0034706033 scopus 로고    scopus 로고
    • and references therein
    • Catalytic enantioselective carbonyl-ene reactions, see eg.: (a) D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras and T. Vojkovsky, J. Am. Chem. Soc., 2000, 122, 7936 and references therein; (b) F. Reichel, X. Fang, S. Yao, M. Ricci and K. A. Jørgensen, Chem. Commun., 1999, 1505; (c) N. Gathergood and K. A. Jørgensen, Chem. Commun., 1999, 1869; (d) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky and S. W. Tregay, J. Am. Chem. Soc., 1998, 120, 5824; (e) Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7936
    • Evans, D.A.1    Tregay, S.W.2    Burgey, C.S.3    Paras, N.A.4    Vojkovsky, T.5
  • 89
    • 0033592231 scopus 로고    scopus 로고
    • Catalytic enantioselective carbonyl-ene reactions, see eg.: (a) D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras and T. Vojkovsky, J. Am. Chem. Soc., 2000, 122, 7936 and references therein; (b) F. Reichel, X. Fang, S. Yao, M. Ricci and K. A. Jørgensen, Chem. Commun., 1999, 1505; (c) N. Gathergood and K. A. Jørgensen, Chem. Commun., 1999, 1869; (d) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky and S. W. Tregay, J. Am. Chem. Soc., 1998, 120, 5824; (e) Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133.
    • (1999) Chem. Commun. , pp. 1505
    • Reichel, F.1    Fang, X.2    Yao, S.3    Ricci, M.4    Jørgensen, K.A.5
  • 90
    • 0033592439 scopus 로고    scopus 로고
    • Catalytic enantioselective carbonyl-ene reactions, see eg.: (a) D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras and T. Vojkovsky, J. Am. Chem. Soc., 2000, 122, 7936 and references therein; (b) F. Reichel, X. Fang, S. Yao, M. Ricci and K. A. Jørgensen, Chem. Commun., 1999, 1505; (c) N. Gathergood and K. A. Jørgensen, Chem. Commun., 1999, 1869; (d) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky and S. W. Tregay, J. Am. Chem. Soc., 1998, 120, 5824; (e) Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133.
    • (1999) Chem. Commun. , pp. 1869
    • Gathergood, N.1    Jørgensen, K.A.2
  • 91
    • 0032540647 scopus 로고    scopus 로고
    • Catalytic enantioselective carbonyl-ene reactions, see eg.: (a) D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras and T. Vojkovsky, J. Am. Chem. Soc., 2000, 122, 7936 and references therein; (b) F. Reichel, X. Fang, S. Yao, M. Ricci and K. A. Jørgensen, Chem. Commun., 1999, 1505; (c) N. Gathergood and K. A. Jørgensen, Chem. Commun., 1999, 1869; (d) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky and S. W. Tregay, J. Am. Chem. Soc., 1998, 120, 5824; (e) Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5824
    • Evans, D.A.1    Burgey, C.S.2    Paras, N.A.3    Vojkovsky, T.4    Tregay, S.W.5
  • 92
    • 0032478649 scopus 로고    scopus 로고
    • Catalytic enantioselective carbonyl-ene reactions, see eg.: (a) D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras and T. Vojkovsky, J. Am. Chem. Soc., 2000, 122, 7936 and references therein; (b) F. Reichel, X. Fang, S. Yao, M. Ricci and K. A. Jørgensen, Chem. Commun., 1999, 1505; (c) N. Gathergood and K. A. Jørgensen, Chem. Commun., 1999, 1869; (d) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky and S. W. Tregay, J. Am. Chem. Soc., 1998, 120, 5824; (e) Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133.
    • (1998) J. Org. Chem. , vol.63 , pp. 2133
    • Gao, Y.1    Lane-Bell, P.2    Vederas, J.C.3
  • 95
    • 0035925220 scopus 로고    scopus 로고
    • Catalytic enantioselective Friedel-Crafts allylation reactions: (a) K. B. Jensen, J. Thorhauge, R. G. Hazell and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 160; (b) W. Zhuang, T. Hansen and K. A. Jørgensen, Chem. Commun., 2001, 347.
    • (2001) Chem. Commun. , pp. 347
    • Zhuang, W.1    Hansen, T.2    Jørgensen, K.A.3
  • 97
    • 0035902842 scopus 로고    scopus 로고
    • Catalytic enantioselective direct Mannich reactions: (a) K. Juhl, N. Gathergood and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 2995; (b) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood and K. A. Jørgensen, Chem. Eur. J., 2003, 9, 2359.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2995
    • Juhl, K.1    Gathergood, N.2    Jørgensen, K.A.3
  • 99
    • 0037139602 scopus 로고    scopus 로고
    • Catalytic enantioselective direct α-amination reactions: (a) K. Juhl and K. A. Jørgensen, J. Am. Chem. Soc., 2002, 124, 2420; (b) M. Marigo, K. Juhl and K. A. Jørgensen, Angew. Chem., Int. Ed., 2003, 42, 1367.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2420
    • Juhl, K.1    Jørgensen, K.A.2
  • 100
    • 0037471191 scopus 로고    scopus 로고
    • Catalytic enantioselective direct α-amination reactions: (a) K. Juhl and K. A. Jørgensen, J. Am. Chem. Soc., 2002, 124, 2420; (b) M. Marigo, K. Juhl and K. A. Jørgensen, Angew. Chem., Int. Ed., 2003, 42, 1367.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1367
    • Marigo, M.1    Juhl, K.2    Jørgensen, K.A.3
  • 101
    • 0034807178 scopus 로고    scopus 로고
    • Catalytic enantioselective aza-Henry reactions: (a) K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf and K. A. Jørgensen, J Am. Chem. Soc., 2001, 123, 5843; (b) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 2992; (c) T. Risgaard, K. V. Gothelf and K. A. Jørgensen, Org. Biomol. Chem., 2003, 1, 153.
    • (2001) J Am. Chem. Soc. , vol.123 , pp. 5843
    • Knudsen, K.R.1    Risgaard, T.2    Nishiwaki, N.3    Gothelf, K.V.4    Jørgensen, K.A.5
  • 102
    • 0035902841 scopus 로고    scopus 로고
    • Catalytic enantioselective aza-Henry reactions: (a) K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf and K. A. Jørgensen, J Am. Chem. Soc., 2001, 123, 5843; (b) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 2992; (c) T. Risgaard, K. V. Gothelf and K. A. Jørgensen, Org. Biomol. Chem., 2003, 1, 153.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2992
    • Nishiwaki, N.1    Knudsen, K.R.2    Gothelf, K.V.3    Jørgensen, K.A.4
  • 103
    • 0037725799 scopus 로고    scopus 로고
    • Catalytic enantioselective aza-Henry reactions: (a) K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf and K. A. Jørgensen, J Am. Chem. Soc., 2001, 123, 5843; (b) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf and K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 2992; (c) T. Risgaard, K. V. Gothelf and K. A. Jørgensen, Org. Biomol. Chem., 2003, 1, 153.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 153
    • Risgaard, T.1    Gothelf, K.V.2    Jørgensen, K.A.3
  • 104
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    • w = 0.06. CCDC reference number 225814. See http://www.rsc.org/suppdata/ob/b3/ b316092k/ for crystallographic data in.cif or other electronic format.


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