Diastereo- and enantioselective syntheses of C2-symmetric 1,n-diamines by nucleophilic addition to dialdehyde-SAMP-hydrazones

Synthesis

Volumn , Issue 17, 2002, Pages 2542-2560

  Enders, Dieter ^a   Meiers, Michaela ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Amines; Asymmetric synthesis; Cerium; Hydrazones; Nucleophilic additions

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; CHEMICAL BONDS; STEREOCHEMISTRY;

ENANTIOMERIC PURITY;

AMINES;

ALDEHYDE DERIVATIVE; DIAMINE; HYDRAZINE 1 AMINO 2 METHOXYMETHYLPYRROLIDINE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BINDING; CHIRALITY; ENANTIOSELECTIVITY; RESIDUE ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036456907     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35628     Document Type: Article

References (152)

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7. For examples see: (a) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754. (b) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209; and literature cited therein. (c) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (d) Blaszis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499. (e) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531; and ref. cited therein. (f) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. (g) Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419. (h) Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
8. For examples see: (a) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754. (b) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209; and literature cited therein. (c) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (d) Blaszis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499. (e) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531; and ref. cited therein. (f) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. (g) Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419. (h) Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
9. For examples see: (a) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754. (b) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209; and literature cited therein. (c) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (d) Blaszis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499. (e) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531; and ref. cited therein. (f) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. (g) Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419. (h) Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
10. For examples see: (a) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754. (b) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209; and literature cited therein. (c) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (d) Blaszis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499. (e) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531; and ref. cited therein. (f) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. (g) Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419. (h) Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
11. For examples see: (a) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754. (b) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209; and literature cited therein. (c) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (d) Blaszis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499. (e) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531; and ref. cited therein. (f) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. (g) Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419. (h) Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
12. For examples see: (a) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754. (b) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209; and literature cited therein. (c) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976. (d) Blaszis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499. (e) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531; and ref. cited therein. (f) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. (g) Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419. (h) Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
13. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
14. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
15. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
16. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
17. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
18. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
19. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
20. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
21. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
22. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
23. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
24. For reviews see also: (a) Jacobsen E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 159. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189 For recent examples see: (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (d) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (e) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (f) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, R.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135. (g) Gamez, P.; Fache, F.; Lemaire, M. Terahedron: Asymmetry 1995, 6, 705. (h) Murata, K.; Ikariya, T. J. Org. Chem. 1999, 64, 2186. (i) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745. (j) Li, X.; Schenkel, L. B.; Kozlowski, M. C. Org. Lett. 2000, 2, 875. (k) Wiberg, K. B.; Bailey, W. F. Tetrahedron Lett. 2000, 41, 9365. (l) Barett, S.; O'Brien, P.; Steffens, H. C.; Towers, T. D.; Voith, M. Tetrahedron 2000, 56, 9633.
25. For examples of 12-diamines as building blocks in ligand construction see: (a) Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037. (c) Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99; Angew. Chem. 1996, 108, 70.
26. For examples of 12-diamines as building blocks in ligand construction see: (a) Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037. (c) Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99; Angew. Chem. 1996, 108, 70.
27. For examples of 12-diamines as building blocks in ligand construction see: (a) Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037. (c) Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99; Angew. Chem. 1996, 108, 70.
28. For examples of 12-diamines as building blocks in ligand construction see: (a) Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037. (c) Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99; Angew. Chem. 1996, 108, 70.
29. For examples see: (a) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002. (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 125; Angew. Chem. 1994, 106, 130. (c) Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, R.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288. (d) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier. J-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
30. For examples see: (a) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002. (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 125; Angew. Chem. 1994, 106, 130. (c) Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, R.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288. (d) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier. J-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
31. For examples see: (a) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002. (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 125; Angew. Chem. 1994, 106, 130. (c) Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, R.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288. (d) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier. J-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
32. For examples see: (a) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002. (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 125; Angew. Chem. 1994, 106, 130. (c) Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, R.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288. (d) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier. J-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
33. For examples see: (a) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002. (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 125; Angew. Chem. 1994, 106, 130. (c) Alexakis, A.; Mangeney, P.; Marek, I.; Rose-Munch, F.; Rose, R.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288. (d) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier. J-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
34. For examples see: (a) Kido, J.; Okamoto, Y.; Brittain, H. G. J. Org. Chem. 1991, 56, 1412. (b) Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. (c) Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J.; Kee, T. P. Tetrahedron: Asymmetry 1995, 6, 2039. (d) Staubach, B.; Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344; Angew. Chem. 1996, 108, 1443.
35. For examples see: (a) Kido, J.; Okamoto, Y.; Brittain, H. G. J. Org. Chem. 1991, 56, 1412. (b) Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. (c) Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J.; Kee, T. P. Tetrahedron: Asymmetry 1995, 6, 2039. (d) Staubach, B.; Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344; Angew. Chem. 1996, 108, 1443.
36. For examples see: (a) Kido, J.; Okamoto, Y.; Brittain, H. G. J. Org. Chem. 1991, 56, 1412. (b) Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. (c) Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J.; Kee, T. P. Tetrahedron: Asymmetry 1995, 6, 2039. (d) Staubach, B.; Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344; Angew. Chem. 1996, 108, 1443.
37. For examples see: (a) Kido, J.; Okamoto, Y.; Brittain, H. G. J. Org. Chem. 1991, 56, 1412. (b) Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. (c) Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J.; Kee, T. P. Tetrahedron: Asymmetry 1995, 6, 2039. (d) Staubach, B.; Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344; Angew. Chem. 1996, 108, 1443.
38. For examples see: (a) Kido, J.; Okamoto, Y.; Brittain, H. G. J. Org. Chem. 1991, 56, 1412. (b) Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. (c) Devitt, P. G.; Mitchell, M. C.; Weetman, J. M.; Taylor, R. J.; Kee, T. P. Tetrahedron: Asymmetry 1995, 6, 2039. (d) Staubach, B.; Buddrus, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1344; Angew. Chem. 1996, 108, 1443.
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47. For recent examples see: (a) Tanaka, K.; Sawanishi, H. Tetrahedron: Asymmetry 2000, 11, 3837. (b) Spielvogel, D.; Kammerer, J.; Keller, M.; Prinzbach, H. Tetrahedron Lett. 2000, 41, 7863. (c) Benedetti, F.; Norbedo, S. Chem. Commun. 2001, 203.
48. For recent examples see: (a) Tanaka, K.; Sawanishi, H. Tetrahedron: Asymmetry 2000, 11, 3837. (b) Spielvogel, D.; Kammerer, J.; Keller, M.; Prinzbach, H. Tetrahedron Lett. 2000, 41, 7863. (c) Benedetti, F.; Norbedo, S. Chem. Commun. 2001, 203.
49. For recent examples see: (a) Tanaka, K.; Sawanishi, H. Tetrahedron: Asymmetry 2000, 11, 3837. (b) Spielvogel, D.; Kammerer, J.; Keller, M.; Prinzbach, H. Tetrahedron Lett. 2000, 41, 7863. (c) Benedetti, F.; Norbedo, S. Chem. Commun. 2001, 203.
50. Diastereoselective synthesis of racemates: (a) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (b) Gómez Aranda, V.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. (c) Bäckvall, J.-E. Tetrahedron Lett. 1975, 2225. (d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420. (e) Schofield, M. H.; Kee, T. P.; Anhaus, J. T.; Schrock, R. R.; Johnson, K. H.; Davis, W. M. Inorg. Chem. 1991, 30, 3595. (f) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
51. Diastereoselective synthesis of racemates: (a) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (b) Gómez Aranda, V.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. (c) Bäckvall, J.-E. Tetrahedron Lett. 1975, 2225. (d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420. (e) Schofield, M. H.; Kee, T. P.; Anhaus, J. T.; Schrock, R. R.; Johnson, K. H.; Davis, W. M. Inorg. Chem. 1991, 30, 3595. (f) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
52. Diastereoselective synthesis of racemates: (a) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (b) Gómez Aranda, V.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. (c) Bäckvall, J.-E. Tetrahedron Lett. 1975, 2225. (d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420. (e) Schofield, M. H.; Kee, T. P.; Anhaus, J. T.; Schrock, R. R.; Johnson, K. H.; Davis, W. M. Inorg. Chem. 1991, 30, 3595. (f) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
53. Diastereoselective synthesis of racemates: (a) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (b) Gómez Aranda, V.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. (c) Bäckvall, J.-E. Tetrahedron Lett. 1975, 2225. (d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420. (e) Schofield, M. H.; Kee, T. P.; Anhaus, J. T.; Schrock, R. R.; Johnson, K. H.; Davis, W. M. Inorg. Chem. 1991, 30, 3595. (f) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
54. Diastereoselective synthesis of racemates: (a) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (b) Gómez Aranda, V.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. (c) Bäckvall, J.-E. Tetrahedron Lett. 1975, 2225. (d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420. (e) Schofield, M. H.; Kee, T. P.; Anhaus, J. T.; Schrock, R. R.; Johnson, K. H.; Davis, W. M. Inorg. Chem. 1991, 30, 3595. (f) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
55. Diastereoselective synthesis of racemates: (a) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (b) Gómez Aranda, V.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. (c) Bäckvall, J.-E. Tetrahedron Lett. 1975, 2225. (d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420. (e) Schofield, M. H.; Kee, T. P.; Anhaus, J. T.; Schrock, R. R.; Johnson, K. H.; Davis, W. M. Inorg. Chem. 1991, 30, 3595. (f) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
56. For recent examples see: (a) Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829. (b) Laschat, S. Liebigs Ann. Recl. 1997, 1. (c) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741; and ref. cited therein. (d) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629. (e) Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chem. Fr. 1997, 134, 299. (f) For a recent example of the synthesis of 13-diamines following this route see: Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
57. For recent examples see: (a) Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829. (b) Laschat, S. Liebigs Ann. Recl. 1997, 1. (c) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741; and ref. cited therein. (d) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629. (e) Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chem. Fr. 1997, 134, 299. (f) For a recent example of the synthesis of 13-diamines following this route see: Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
58. For recent examples see: (a) Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829. (b) Laschat, S. Liebigs Ann. Recl. 1997, 1. (c) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741; and ref. cited therein. (d) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629. (e) Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chem. Fr. 1997, 134, 299. (f) For a recent example of the synthesis of 13-diamines following this route see: Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
59. For recent examples see: (a) Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829. (b) Laschat, S. Liebigs Ann. Recl. 1997, 1. (c) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741; and ref. cited therein. (d) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629. (e) Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chem. Fr. 1997, 134, 299. (f) For a recent example of the synthesis of 13-diamines following this route see: Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
60. For recent examples see: (a) Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829. (b) Laschat, S. Liebigs Ann. Recl. 1997, 1. (c) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741; and ref. cited therein. (d) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629. (e) Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chem. Fr. 1997, 134, 299. (f) For a recent example of the synthesis of 13-diamines following this route see: Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
61. For recent examples see: (a) Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829. (b) Laschat, S. Liebigs Ann. Recl. 1997, 1. (c) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741; and ref. cited therein. (d) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629. (e) Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chem. Fr. 1997, 134, 299. (f) For a recent example of the synthesis of 13-diamines following this route see: Guerra, F. M.; Mish, M. R.; Carreira, E. M. Org. Lett. 2000, 2, 4265.
62. For recent examples see: (a) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. (b) Corey, E. J.; Lee, D.-H.; Sarshan, S. Tetrahedron: Asymmetry 1995, 6, 3. (c) Busacca, C. A.; Campbell, S.; Dong, Y.: Grossbach, D.; Ridges, M.; Smith, L.; Spinelli, E. J. Org. Chem. 2000, 65, 4753. (d) Dell'Erba, C.; Novi, M.; Petrillo, G.; Spinelli, D.; Tavani, C. Tetrahedron 1996, 52, 3313.
63. For recent examples see: (a) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. (b) Corey, E. J.; Lee, D.-H.; Sarshan, S. Tetrahedron: Asymmetry 1995, 6, 3. (c) Busacca, C. A.; Campbell, S.; Dong, Y.: Grossbach, D.; Ridges, M.; Smith, L.; Spinelli, E. J. Org. Chem. 2000, 65, 4753. (d) Dell'Erba, C.; Novi, M.; Petrillo, G.; Spinelli, D.; Tavani, C. Tetrahedron 1996, 52, 3313.
64. For recent examples see: (a) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. (b) Corey, E. J.; Lee, D.-H.; Sarshan, S. Tetrahedron: Asymmetry 1995, 6, 3. (c) Busacca, C. A.; Campbell, S.; Dong, Y.: Grossbach, D.; Ridges, M.; Smith, L.; Spinelli, E. J. Org. Chem. 2000, 65, 4753. (d) Dell'Erba, C.; Novi, M.; Petrillo, G.; Spinelli, D.; Tavani, C. Tetrahedron 1996, 52, 3313.
65. For recent examples see: (a) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607. (b) Corey, E. J.; Lee, D.-H.; Sarshan, S. Tetrahedron: Asymmetry 1995, 6, 3. (c) Busacca, C. A.; Campbell, S.; Dong, Y.: Grossbach, D.; Ridges, M.; Smith, L.; Spinelli, E. J. Org. Chem. 2000, 65, 4753. (d) Dell'Erba, C.; Novi, M.; Petrillo, G.; Spinelli, D.; Tavani, C. Tetrahedron 1996, 52, 3313.
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77. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
78. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
79. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
80. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
81. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
82. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
83. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
84. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
85. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
86. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
87. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
88. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
89. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
90. For examples see: (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem Rev. 1994, 94, 2483. (b) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 35, 9241. (c) Skarzewski, J.; Gupta, A. Tetrahedron:' Asymmetry 1997, 8, 1861. (d) Lee, S.-G.; Lee, S. H.; Song, C.; Chung, B. Y. Tetrahedron: Asymmetry 1999, 10, 1795. (e) Lim, C.-C.; Mok, K. F.; Sim, K. Y.; Leung, P.-H. Tetrahedron: Asymmetry 1997, 8, 2045. (f) Lee, S.-G.; Lim, C. W.; Lee, J. K.; Jung, O.-S.; Lee, Y.-A. Tetrahedron: Asymmetry 2000, 11, 4709. (g) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556. (h) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Org. Lett. 2000, 2, 1243. (i) De Sousa, S. E.; O'Brien, P.; Poumelle, P. J. Chem. Soc., Perkin Trans 1 1998, 1483. (j) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans 1 1997, 511. (k) Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1990, 505. (l) Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045. (m) Stingl, K.; Martens, J. Liebigs Ann. Chem. 1994, 243. (n) Valasinas, A.; Frydman, B.; Friedmann, H. C. J. Org Chem. 1992, 57, 2158.
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97. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
98. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
99. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
100. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
101. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
102. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
103. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
104. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
105. For examples see: (a) Taniguchi, N.; Uemura, M. Synlett 1997, 51. (b) Baruah, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1995, 36, 6747. (c) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609. (d) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647. (e) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685; Angew. Chem. 1994, 106, 719. (f) Yanada, R.; Negoro, N.; Okaniwa, M.; Miwa, Y.; Taga, T.; Yanada, K.; Fujita, T. Synlett 1999, 5, 537. (g) Campos, P. J.; Arranz, J.; Rodríguez, M. A. Tetrahedron 2000, 56, 7285. (h) Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829.
106. (a) Enders, D.; Wiedemann, J. Synthesis 1996, 1443.
107. (b) Lucet, D.; Toupet, L.; Le Gall, T.; Mioskowski, C. J. Org. Chem. 1997, 62, 2682.
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118. For recent reviews on the 12-addition of organometallic reagents to the CN double bond see: (a) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442. (f) Alvaro, G.; Savoia, D. Synlett 2002, 651.
119. For recent reviews on the 12-addition of organometallic reagents to the CN double bond see: (a) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442. (f) Alvaro, G.; Savoia, D. Synlett 2002, 651.
120. For recent reviews on the 12-addition of organometallic reagents to the CN double bond see: (a) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442. (f) Alvaro, G.; Savoia, D. Synlett 2002, 651.
121. For recent reviews on the 12-addition of organometallic reagents to the CN double bond see: (a) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442. (f) Alvaro, G.; Savoia, D. Synlett 2002, 651.
122. For recent reviews on the 12-addition of organometallic reagents to the CN double bond see: (a) Denmark, S. E.; Nicaise, O. J.-C. Chem. Commun. 1996, 999. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (e) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442. (f) Alvaro, G.; Savoia, D. Synlett 2002, 651.
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