2,8′-Disubstituted-1,1′-binaphthyls: A new pattern in chiral ligands

Chemistry - A European Journal

Volumn 8, Issue 20, 2002, Pages 4633-4648

  Vyskočil, Štěpán ^a,b   Meca, Luděk ^b   Tišlerová, Iva ^b   Císařová, Ivana ^b   Polášek, Miroslav ^c   Harutyunyan, Syuzanna R ^d   Belokon, Yuri N ^d   Stead, Russel M J ^e   Farrugia, Louis ^a   Lockhart, Stephen C ^a   Mitchell, William L ^f   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b CHARLES UNIVERSITY   (Czech Republic)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^d A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^e UNIVERSITY OF LEICESTER   (United Kingdom)

^f GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Amination; Binaphthyls; Chiral resolution; Chirality; Suzuki coupling

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CRYSTALLIZATION; HYDROLYSIS; ISOMERS; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

FUNCTIONAL GROUP TRANSFORMATIONS;

ORGANIC COMPOUNDS;

1,1' BINAPHTHYL DERIVATIVE; 2 AMINO 2' HYDROXY 1,1' BINAPHTHYL; 2 METHOXY 2' (DIPHENYLPHOSPHINO) 1,1' BINAPHTHYL; ACRYLIC ACID DERIVATIVE; GLUTAMIC ACID; GLYCINE; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHIRALITY; HYDROLYSIS; PHASE TRANSITION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037131454     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021018)8:20<4633::AID-CHEM4633>3.0.CO;2-N     Document Type: Article

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32. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
33. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
34. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
35. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
36. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
37. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
38. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
39. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
40. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
41. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
42. For ligands derived from NOBIN, see: a) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837; b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649; c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360: d) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37; e) J. J. van Veldhuizen, S. B. Garber, J. S. Kingsbury, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 4954; f) W. Tang, X. Hu, X. Zhang, Tetrahedron Lett. 2002, 43, 3075: for the corresponding methyl ether and imines derived from it, see: g) H.-J. Knölker, H. Hermann, Angew. Chem. 1996, 108, 363; Angew. Chem. Int. Ed. Engl. 1996, 35, 341; h) B. Hungerhoff, P. Metz, Tetrahedron 1999, 55, 14941: For recent applications of NOBIN itself in asymmetric synthesis, see: i) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, Š. Vyskočil, H. B. Kagan, Tetrahedron: Asymmetry 1999, 10, 1723; j) Y. N. Belokon, K. A. Kochetkov, T. D. Churrkkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, Š. Vyskočil, H. B. Kagan, J. Org. Chem. 2000, 65, 7041; k) Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, O. V. Larionov, S. R. Harutjunan, Š. Vyskočil, M. North, H. B. Kagan, Angew. Chem. 2001, 113, 2002; Angew. Chem. Int. Ed. 2001, 40, 1948.
43. a) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc, 1991, 113, 9887; for a recent contribution, see: b) T. Hayashi, S. Hirate, K. Kitayama, H. Tsuji, A. Torii, Y. Uozumi, J. Org. Chem. 2001, 66, 1441; for reviews, see: c) T. Hayashi, Acta Chem. Scand. 1996, 50, 259; d) T. Hayashi, Acc. Chem. Res. 2000, 33, 354.
44. a) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc, 1991, 113, 9887; for a recent contribution, see: b) T. Hayashi, S. Hirate, K. Kitayama, H. Tsuji, A. Torii, Y. Uozumi, J. Org. Chem. 2001, 66, 1441; for reviews, see: c) T. Hayashi, Acta Chem. Scand. 1996, 50, 259; d) T. Hayashi, Acc. Chem. Res. 2000, 33, 354.
45. a) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc, 1991, 113, 9887; for a recent contribution, see: b) T. Hayashi, S. Hirate, K. Kitayama, H. Tsuji, A. Torii, Y. Uozumi, J. Org. Chem. 2001, 66, 1441; for reviews, see: c) T. Hayashi, Acta Chem. Scand. 1996, 50, 259; d) T. Hayashi, Acc. Chem. Res. 2000, 33, 354.
46. a) Y. Uozumi, T. Hayashi, J. Am. Chem. Soc, 1991, 113, 9887; for a recent contribution, see: b) T. Hayashi, S. Hirate, K. Kitayama, H. Tsuji, A. Torii, Y. Uozumi, J. Org. Chem. 2001, 66, 1441; for reviews, see: c) T. Hayashi, Acta Chem. Scand. 1996, 50, 259; d) T. Hayashi, Acc. Chem. Res. 2000, 33, 354.
47. a) Š. Vyskočil, M. Smrčína, V. Hanuš, J. Polášek, P. Kočovský, J. Org. Chem. 1998, 63, 7738;
48. b) Š. Vyskočil, M. Smrčina, P. Kočovský, Tetrahedron Lett. 1998, 39, 9298;
49. c) P. Kočovský, Š. Vyskočil, I. Císařová, J. Sejbal, I. Tišlerová, M. Smrčina, G. C. Lloyd-Jones, S. C. Stephen, C. P. Butts, M. Murray, V. Langer, J. Am. Chem. Soc. 1999, 121, 7714:
50. d) A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4369;
51. e) X. Hu, H. Chen, X, Zhang, Angew. Chem. 1999, 111, 3720: Angew. Chem. Int. Ed. 1999, 38, 3518;
52. e) X. Hu, H. Chen, X, Zhang, Angew. Chem. 1999, 111, 3720: Angew. Chem. Int. Ed. 1999, 38, 3518;
53. f) J. M. Fox, X. Huang, A. Chieffi, A. S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 1360;
54. g) G. C. Lloyd-Jones, S. C. Stephen, M. Murray, C. P. Butts, Š. Vyskočil, P. Kočovský, Chem. Eur. J. 2000, 6, 4348;
55. h) I. J. S. Fairlamb, G. C. Lloyd-Jones, Š. Vyskočil, P. Kočovský, Chem. Eur. J. 2002, 8, 4443.
56. 3-catalyzed allylic substitution were rather disappointing (< 17% ee): P. Lustenberger, F. Diederich, Helv. Chim. Acta 2000, 83, 2865; b) In our opinion, this result may originate from the formation of oligomeric Pd species instead of the expected, rigid chelate.
57. 3-catalyzed allylic substitution were rather disappointing (< 17% ee): P. Lustenberger, F. Diederich, Helv. Chim. Acta 2000, 83, 2865; b) In our opinion, this result may originate from the formation of oligomeric Pd species instead of the expected, rigid chelate.
58. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
59. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
60. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
61. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
62. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
63. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
64. For early work on racemic 8,8′-disubstituted 1,1′-binaphthyls, see: a) Y. Badar, A. S. Cooke, M. M. Harris, J. Chem. Soc. 1965, 165; b) H. E. Harris, M. M. Harris, R. Z. Mazengo, S. Shing, J. Chem. Soc. Perkin Trans. 1 1974, 1059; c) M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin 2 1978, 304; d) J. D. Korp, I. Bernal, M. M. Harris, P. K. Patel, J. Chem. Soc. Perkin Trans. 2 1981, 1621; e) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; for the resolved 8,8-diol, see: f) D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1995, 60, 6599; g) K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem. 1995, 60, 1914.
65. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
66. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
67. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
68. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
69. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
70. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
71. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
72. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
73. 8,8′-Diol: ref. [10f.g] and the following: a) S. P. Artz, M. P. deGrandpre, D. J. Cram, J. Org. Chem. 1985, 50, 1486; b) K. Matsumoto, H. Ohta, Tetrahedron Lett. 1991, 32, 4729; c) K. Fuji, X. Yang, K. Tanaka, N. Asakawa, X. Hao, Tetrahedron Lett. 1996, 37, 7373; d) K. Tanaka, N. Asakawa, M. Nuruzzaman, K. Fuji, Tetrahedron: Asymmetry 1997, 8, 3637; 8,8′-Bisoxazoline: ref. [11b] and the following: e) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869; f) A. I. Meyers, K. A. Lutomski, J. Am. Chem. Soc. 1982, 104, 879; g) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412; h) S. V. Kolotuchin, A. I. Meyers, J. Org. Chem. 1999, 64, 7921; 8,8′-MOP; i) K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Tetrahedron Lett. 1998, 39, 6323.
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110. a) H. H. Hodgson, J. S. Whitehurst, J. Chem. Soc. 1947, 80; b) D. Seyferth, S. C. Vick, J. Organomet. Chem. 1977, 141, 173; Improved protocols with naphtho[1,8-de]triazine: c) C. W. Rees, R. C. Starr, J. Chem. Soc. C 1969, 756; d) M. Kuroda, J. Nakayama, M. Hoshino, N. Furusho, T. Kawata, S. Ohba, Tetrahedron, 1993, 49, 3735.
111. a) H. H. Hodgson, J. S. Whitehurst, J. Chem. Soc. 1947, 80; b) D. Seyferth, S. C. Vick, J. Organomet. Chem. 1977, 141, 173; Improved protocols with naphtho[1,8-de]triazine: c) C. W. Rees, R. C. Starr, J. Chem. Soc. C 1969, 756; d) M. Kuroda, J. Nakayama, M. Hoshino, N. Furusho, T. Kawata, S. Ohba, Tetrahedron, 1993, 49, 3735.
112. a) H. H. Hodgson, J. S. Whitehurst, J. Chem. Soc. 1947, 80; b) D. Seyferth, S. C. Vick, J. Organomet. Chem. 1977, 141, 173; Improved protocols with naphtho[1,8-de]triazine: c) C. W. Rees, R. C. Starr, J. Chem. Soc. C 1969, 756; d) M. Kuroda, J. Nakayama, M. Hoshino, N. Furusho, T. Kawata, S. Ohba, Tetrahedron, 1993, 49, 3735.
113. 2], the reduction product 20 dominated the product mixture. Finally, the temperature also proved important since at 50-70°C, formation of the reduction product 20 and of 2,2′-dimethoxy-1,1′-binaphthyl was promoted at the expense of 18.
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115. Identical with an authentic sample: a) J. A. Berson, M. A. Greenbaum, J. Am. Chem. Soc. 1958, 80, 653; b) J. M. Wilson, D. J. Cram, J. Org. Chem. 1984, 49, 4930; c) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670; d) B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276; e) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165; f) C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chim. Fr 1997, 134, 399.
116. Identical with an authentic sample: a) J. A. Berson, M. A. Greenbaum, J. Am. Chem. Soc. 1958, 80, 653; b) J. M. Wilson, D. J. Cram, J. Org. Chem. 1984, 49, 4930; c) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670; d) B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276; e) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165; f) C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chim. Fr 1997, 134, 399.
117. Identical with an authentic sample: a) J. A. Berson, M. A. Greenbaum, J. Am. Chem. Soc. 1958, 80, 653; b) J. M. Wilson, D. J. Cram, J. Org. Chem. 1984, 49, 4930; c) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670; d) B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276; e) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165; f) C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chim. Fr 1997, 134, 399.
118. Identical with an authentic sample: a) J. A. Berson, M. A. Greenbaum, J. Am. Chem. Soc. 1958, 80, 653; b) J. M. Wilson, D. J. Cram, J. Org. Chem. 1984, 49, 4930; c) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670; d) B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276; e) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165; f) C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chim. Fr 1997, 134, 399.
119. Identical with an authentic sample: a) J. A. Berson, M. A. Greenbaum, J. Am. Chem. Soc. 1958, 80, 653; b) J. M. Wilson, D. J. Cram, J. Org. Chem. 1984, 49, 4930; c) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670; d) B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276; e) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165; f) C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chim. Fr 1997, 134, 399.
120. Identical with an authentic sample: a) J. A. Berson, M. A. Greenbaum, J. Am. Chem. Soc. 1958, 80, 653; b) J. M. Wilson, D. J. Cram, J. Org. Chem. 1984, 49, 4930; c) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670; d) B. H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc. 1993, 115, 9276; e) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165; f) C. D. Braddock, S. C. Tucker, J. M. Brown, Bull. Soc. Chim. Fr 1997, 134, 399.
121. a) For a related insertion of Pd into the aromatic C-H bond, see, for example: B. Martín-Matute, C. Mateo, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2001, 7, 2341 and references therein;
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143. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
144. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
145. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
146. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
147. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
148. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
149. Toda's original protocol suffered from less than satisfactory enantioselectivity. A simple switching of the solvent employed for crystallization from methanol to acetonitrile dramatically improved the resolution of BINOL: a) D. Cai, D. L. Hughes, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7991; for other recent applications of this method, see ref. [5m] and the following: b) J. Reeder, P. P. Castro, C. B. Knobler, E. Martinborough, L. Owens, F. Diederich, J. Org. Chem. 1994, 59, 3151; c) Q.-S. Hu, D. R. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123; d) Š. Vyskočil, M. Smrčina, M. Lorenc, I. Tišlerová, R. D. Brooks, J. J. Kulagowski, V. Langer, L. Farrugia, P. Kočovský, J. Org. Chem. 2001, 66, 1351; resolution with -1-phenylethylamine: e) M. Periasamy, L. Venkatraman, S. Sivakumar, N. Sampathkumar, C. R. Ramanathan, J. Org. Chem. 1999, 64, 7643; f) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319; for mechanistic understanding see: g) N. M. Maier, S. Schefzick, G. M. Lombardo, M. Feliz, K. Rissanen, W. Lindner, K. B. Lipkowitz, J. Am. Chem. Soc. 2002, 124, 8611.
150. G. Bringmann, M. Heubes, M. Breuning, L. Göbel, M. Ochse, B. Schöner, O. Schupp, J. Org. Chem. 2000, 65, 722.
151. All quantum chemistry calculations were performed with the Gaussian 98 package of programs. Full transition-state optimizations have been performed by using the STQN method. Second derivative calculations established the nature of stationary point (one negative eigenvalue). The reaction path was confirmed by IRC calculations.
152. Preliminary X-ray data indicate that the chiral axis in the 1,2′-isomer 17 is rather longer (1.570 Å) than that in 18 (1.496 Å). This structural feature is apparently reflected in the lower barriers to racemization of 16, 17, and 35 (Tables 3 and 4).
153. a) For the quantum chemistry calculations of the T-type H-π interactions in a dimer of benzene and related systems, see: P. Hobza, H. L. Selzle, E. W. Schlag, J. Am. Chem. Soc. 1994, 116, 3500;
154. b) In the case of 24, the T-type interaction is evidenced by an enhanced electron density along the axis connecting the ortho-carbon of the phenyl group with a position of the naphthalene unit close to C(5′) (i.e., between C29 and C15 in Figure 2), observed by high-resolution X-ray crystallography. Details of this study and further confirmation of this interaction provided by quantum chemistry calculations will be published elsewhere.
155. 1H NMR spectroscopy revealed a free rotation of the benzene rings of the imine moiety in the solution from room temperature to ca. -60 °C. Around ca. -50 °C, minimal broadening of the individual signals was observed, suggesting that the coalescent temperature will lay well below the reach of the instrument.
156. 2 solution by a slow diffusion of hexane.
157. Interestingly, the X-ray crystallography of -(+)-18 (Figure S4, Supporting Information) revealed the presence of two molecules in the cell, which differ slightly from each other. Thus, for instance, the dihedral angle about the chiral axis in the two molecules (C2-C1-C1′-C2′) differs by 7.9°, being 77.6° and 69.7°, respectively. Interestingly, this angle in the case of racemic (±)-18 is 89.7°.
158. No racemization had occurred during these transformations, as revealed by chiral HPLC (note that racemates were available for comparison).
159. For another use of complex 39 in a disatereoselective (but not enantioselective) alkylation by Michael addition, see: a) V. A. Soloshonok, C. Cai, V. J. Hruby, Tetrahedron Lett. 2000, 41, 9645. For a further modofication that involves a (stoichiometric) chiral auxiliary, see: b) C. Cai, V. A. Soloshonok, V. J. Hruby, J. Org. Chem. 2001, 66, 1339; c) V. A. Soloshonok, X. Tang, V. J. Hruby, L. Van Meervelt, Org. Lett. 2001, 3, 341.
160. For another use of complex 39 in a disatereoselective (but not enantioselective) alkylation by Michael addition, see: a) V. A. Soloshonok, C. Cai, V. J. Hruby, Tetrahedron Lett. 2000, 41, 9645. For a further modofication that involves a (stoichiometric) chiral auxiliary, see: b) C. Cai, V. A. Soloshonok, V. J. Hruby, J. Org. Chem. 2001, 66, 1339; c) V. A. Soloshonok, X. Tang, V. J. Hruby, L. Van Meervelt, Org. Lett. 2001, 3, 341.
161. For another use of complex 39 in a disatereoselective (but not enantioselective) alkylation by Michael addition, see: a) V. A. Soloshonok, C. Cai, V. J. Hruby, Tetrahedron Lett. 2000, 41, 9645. For a further modofication that involves a (stoichiometric) chiral auxiliary, see: b) C. Cai, V. A. Soloshonok, V. J. Hruby, J. Org. Chem. 2001, 66, 1339; c) V. A. Soloshonok, X. Tang, V. J. Hruby, L. Van Meervelt, Org. Lett. 2001, 3, 341.
162. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
163. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
164. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
165. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
166. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
167. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
168. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
169. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
170. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
171. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
172. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
173. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
174. For selected recent catalytic methods of enantioselective alkylation of glycine-derived enolates, see, eg: a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228; c) T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 1515; d) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329; e) S. Jew, B.-S. Jeong. M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244; f) U. Kazamier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067; g) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621: Angew. Chem. Int. Ed. 2002, 41, 1551; h) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956; Angew. Chem. Int. Ed. 2002, 41, 2832; for recent methods using chiral auxiliary, see, for example: i) F.-Y. Chen, B.-J. Uang, J. Org. Chem. 2001, 66, 3650; j) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López, R. González-Muniz, J. Org. Chem. 2001, 66, 3538; for the factors governing the α-carbon acidity of glycine derivatives, see: k) A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949.
175. In preliminary experiments, we have found -iso-NOBIN [-(-)-26] slightly less effective in alkylation of 39, giving (S)-phenyl alanine 87% ee under the same conditions (solid NaOH, RT, 13 min, 40%): Y. N. Belokon, S. R. Harutyunyan, Š. Vyskočil, P. Kočovský, unpublished results.
176. The formamide analogue of acetamide 1i catalyzed the formation of 41 (RT, 6 min: 65%) but gave a practically racemic product (compare with 55% ee for 1i), showing the importance of the nature of the amide.
177. [6k] indicates that racemization of the monoalkylated product, such as 41, that would also involve second enolization, is minimal.
178. Preliminary crystallographic data show the complex 39 to be essentially flat with minor Ni puckering.
179. For the concept of nonlinear effect, see: a) C. Puchot, O. Samuel, E. Dunach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc. 1986, 108, 2353; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Ed. Engl. 1998, 37, 2922 (an overview).
180. For the concept of nonlinear effect, see: a) C. Puchot, O. Samuel, E. Dunach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc. 1986, 108, 2353; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Ed. Engl. 1998, 37, 2922 (an overview).
181. For the concept of nonlinear effect, see: a) C. Puchot, O. Samuel, E. Dunach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc. 1986, 108, 2353; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Ed. Engl. 1998, 37, 2922 (an overview).
182. "Processing of X-ray Diffraction Data Collected in Oscillation Mode": Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307.
183. R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426.
184. R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33.
185. G. M. Sheldrick, SHELXS-97, a program for crystal structure solution University of Göttingen (Germany), 1997, Release 97-2.