Small peptides as ligands for catalytic asymmetric alkylations of olefins. Rational design of catalysts or of searches that lead to them?

Chemical Communications

Volumn , Issue 16, 2004, Pages 1779-1785

  Hoveyda, Amir H ^a,b,c,d,e   Hird, Alexander W ^a,f,g   Kacprzynski, Monica A ^a,f,h  

^a BOSTON COLLEGE   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c YALE UNIVERSITY   (United States)

^d AMERICAN CANCER SOCIETY   (United States)

^e Pfizer Central Research   (United States)

^f Boston College ^*

^g UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^h RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINO ACID DERIVATIVE; COPPER; LIGAND; METAL COMPLEX; NICKEL; PEPTIDE; ZIRCONIUM;

ADDITION REACTION; ALKYLATION; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATION; PROTEIN STRUCTURE; REACTION ANALYSIS; REVIEW;

EID: 4644299863     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b401123f     Document Type: Review

References (63)

1. The word "design" is described in the Unabridged Webster English Dictionary as follows: "To conceive and plan out in mind".
2. (a) A. H. Hoveyda and J. P. Morken, Angew. Chem. Int. Ed., 1996, 35, 1262-1284;
3. (b) A. H. Hoveyda and N. M. Heron in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin and Heidelberg, 1999, pp. 431-454;
4. (c) I. Marek, Perkin Trans. 1, 1999, 535-544;
5. (d) See also: J. de Armas, S. P. Kolis and A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 5977-5983;
6. (e) R. R. Cesati III, J. de Armas and A. H. Hoveyda, Org. Lett., 2002, 4, 395-398.
7. M. T. Didiuk, C. W. Johannes, J. P. Morken and A. H. Hoveyda, J. Am. Chem. Soc., 1995, 117, 7097-7104.
8. (a) A. F. Houri, Z. Xu, D. A. Cogan and A. H. Hoveyda, J. Am. Chem. Soc., 1995, 117, 2943-2944;
9. (b) Z. Xu, C. W. Johannes, A. F. Houri, D. S. La, D. A. Cogan, G. E. Hofilena and A. H. Hoveyda, J. Am. Chem. Soc., 1997, 119, 10302-10316;
10. (c) See also: C. W. Johannes, M. S. Visser and G. S. Weatherhead, J. Am. Chem. Soc., 1998, 120, 8340-8347.
11. (a) D. Y. Kondakov and E. Negishi, J. Am. Chem. Soc., 1995, 117, 10771-10772;
12. (b) D. Y. Kondakov and E. Negishi, J. Am. Chem. Soc., 1996, 118, 1577-1578;
13. (c) D. Y. Kondakov, S. Wang and E. Negishi, Tetrahedron Lett., 1996, 37, 3803-3806;
14. (d) P. Wipf and S. Ribe, Org. Lett., 2000, 2, 1713-1716.
15. E. Gomez-Bengoa, N. M. Heron, M. T. Didiuk, C. A. Luchaco and A. H. Hoveyda, J. Am. Chem. Soc., 1998, 120, 7649-7650.
16. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
17. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
18. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
19. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
20. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
21. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
22. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
23. For a review on the effect of additives on asymmetric catalytic transformations, see: (a) E. M. Vogel, H. Groger and M. Shibasaki, Angew. Chem. Int. Ed., 1999, 38, 1570-1577. For additional recent examples, see (b) H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 2000, 122, 8180-8186; (c) S. Yamasaki, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 1256-1257; (d) S. Kobayashi, H. Ishitani, Y. Yamashita, M. Ueno and H. Shimizu, Tetrahedron, 2001, 57, 861-866; (e) S. Ribe and P. Wipf, Chem. Commun., 2001, 299-307; (f) X. Teng, D. R. Cefalo, R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 10779-10784; (g) N. S. Josephsohn, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4018-4019; (h) H. Deng, J-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 9031-9034.
24. (a) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper and A. H. Hoveyda, Angew. Chem. Int. Ed., 1996, 35, 1668-1671;
25. (b) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, Angew. Chem. Int. Ed., 1997, 36, 1704-1707;
26. (c) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 4284-4285;
27. (d) J. R. Porter, W. G. Wirschun, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 2657-2658.
28. For a discussion of various perceptions regarding catalyst "design" and the significance of modular peptide-based catalysts, see: A. H. Hoveyda, in Handbook of Combinatorial Chemistry, ed. K. C. Nicolaou, R. Hanko and W. Hartwig, Wiley-VCH, Weinheim, 2002, pp. 991-1016.
29. N. S. Josephsohn, K. W. Kuntz, M. L. Snapper and A. H. Hoveyda, J. Am. Chem. Soc., 2001, 123, 11594-11599.
30. (a) M. van Klaveren, E. S. M. Persson, A. del Villar, D. M. Grove, J.-E. Backvall and G. van Koten, Tetrahedron Lett., 1995, 36, 3059-3062;
31. (b) F. Dubner and P. Knochel, Angew. Chem. Int. Ed. Engl., 1999, 38, 379-381;
32. (c) F. Dubner and P. Knochel, Tetrahedron Lett., 2000, 41, 9233-9237;
33. (d) G. J. Meuzelaar, A. S. E. Karlstorm, M. van Klaveren, E. S. M. Persson, A. del Villar, G. van Koten and J-E. Backvall, Tetrahedron, 2000, 56, 2895-2903;
34. (e) H. Malda, A. W. van Zijl, L. A. Arnold and B. L. Feringa, Org. Lett., 2001, 3, 1169-1171;
35. (f) A. S. E. Karlstorm, F. F. Huerta, G. J. Meuzelaar and J-E. Backvall, Synlett., 2001, 923-926.
36. For reports that have appeared subsequent to our work (ref. 12), see (g) S. Ongeri, U. Piarulli, M. Roux, C. Monti and C. Gennari, Helv. Chim. Acta, 2002, 85, 3388-3399; (h) A. Alexakis and K. Coroset, Org. Lett., 2002, 4, 4147-4149; (i) W-J. Shi, L-X. Wang, Y. Fu, S-F. Zhu and Q-L. Zhou, Tetrahedron: Asymmetry, 2003, 14, 3867-3872.
37. For reports that have appeared subsequent to our work (ref. 12), see (g) S. Ongeri, U. Piarulli, M. Roux, C. Monti and C. Gennari, Helv. Chim. Acta, 2002, 85, 3388-3399; (h) A. Alexakis and K. Coroset, Org. Lett., 2002, 4, 4147-4149; (i) W-J. Shi, L-X. Wang, Y. Fu, S-F. Zhu and Q-L. Zhou, Tetrahedron: Asymmetry, 2003, 14, 3867-3872.
38. For reports that have appeared subsequent to our work (ref. 12), see (g) S. Ongeri, U. Piarulli, M. Roux, C. Monti and C. Gennari, Helv. Chim. Acta, 2002, 85, 3388-3399; (h) A. Alexakis and K. Coroset, Org. Lett., 2002, 4, 4147-4149; (i) W-J. Shi, L-X. Wang, Y. Fu, S-F. Zhu and Q-L. Zhou, Tetrahedron: Asymmetry, 2003, 14, 3867-3872.
39. C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy and A. H. Hoveyda, Angew. Chem. Int. Ed., 2001, 40, 1456-1460.
40. For recent reviews of catalytic asymmetric conjugate additions of alkylmetals to unsaturated carbonyls, see: (a) N. Kraus and A. Hoffman-Roder, Synthesis, 2001, 171-196; (b) A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221-3236; (c) B. L. Feringa, R. Naaz, R. Imbos and L. A. Arnold in Modern Organocopper Chemistry, ed. N. Krause, Wiley-VCH, Weinheim, 2002, pp. 224-258.
41. For recent reviews of catalytic asymmetric conjugate additions of alkylmetals to unsaturated carbonyls, see: (a) N. Kraus and A. Hoffman-Roder, Synthesis, 2001, 171-196; (b) A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221-3236; (c) B. L. Feringa, R. Naaz, R. Imbos and L. A. Arnold in Modern Organocopper Chemistry, ed. N. Krause, Wiley-VCH, Weinheim, 2002, pp. 224-258.
42. For recent reviews of catalytic asymmetric conjugate additions of alkylmetals to unsaturated carbonyls, see: (a) N. Kraus and A. Hoffman-Roder, Synthesis, 2001, 171-196; (b) A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221-3236; (c) B. L. Feringa, R. Naaz, R. Imbos and L. A. Arnold in Modern Organocopper Chemistry, ed. N. Krause, Wiley-VCH, Weinheim, 2002, pp. 224-258.
43. S. J. Degrado, H. Mizutani and A. H. Hoveyda, J. Am. Chem. Soc., 2001, 123, 755-756.
44. S. J. Degrado, H. Mizutani and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 13362-13363.
45. C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 8192-8193.
46. T. Hayashi, T. Senda and M. Ogasawara, J. Am. Chem. Soc., 2000, 122, 10716-10717.
47. 2Zn to the six-membered ring nitroalkene in Scheme 5 in 95% ee), see: A. Alexakis, C. Benhaim, S. Rosset and M. Humam, J. Am. Chem. Soc., 2002, 124, 5262-5263.
48. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
49. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
50. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
51. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
52. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
53. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
54. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
55. For representative key studies, see: (a) M. van Klaveren, F. Lambert, J. F. M. Eijkelkamp, D. M. Grove and G. van Koten, Tetrahedron Lett., 1994, 35, 6135-6138; (b) E. L. Strangeland and T. Sammakia, Tetrahedron, 1997, 53, 16503-16510; (c) S. M. W. Bennet, S. M. Brown, J. P. Muxworthy and S. Woodward, Tetrahedron Lett., 1999, 40, 1767-1770; (d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz and B. L. Feringa, Tetrahedron, 2000, 56, 2879-2888; (e) I. H. Escher and A. Pfaltz, Tetrahedron, 2000, 56, 2879-2888; (f) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen and C. Benhaim, Synlett, 2001, 1375-1378; (g) L. A. Arnold, R. Naasz, A. J. Minaard and B. L. Feringa, J. Org. Chem., 2002, 67, 7244-7254; (h) I. J. Krauss and J. L. Leighton, Org. Lett., 2003, 5, 3201-3203.
56. H. Mizutani, S. J. Degrado and A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 779-781.
57. (a) S. B. Garber, J. S. Kingsbury, B. L. Gray and A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 8168-8179;
58. (b) A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. Kingsbury and J. P. A. Harrity, Org. Biol. Chem., 2004, 2, 8-23.
59. R. R. Cestai III, J. de Armas and A. H. Hoveyda, J. Am. Chem. Soc., 2004, 126, 96-101.
60. A. W. Hird and A. H. Hoveyda, Angew. Chem. Int. Ed., 2003, 42, 1276-1279.
61. K. E. Murphy and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4690-4691.
62. M. A. Kacrpzynski and A. H. Hoveyda, J. Am. Chem. Soc., 2004, 126, in press.
63. These experiments were carried out by Dr. Hirotake Mizutani.