A new type of C2-symmetric bisphospine ligands with a cyclobutane backbone: Practical synthesis and application

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1349-1351

  Zhao, Dongbo ^a   Ding, Kuiling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN; CYCLOBUTANE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; HYDROGEN BOND; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141721329     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034299c     Document Type: Article

References (34)

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20. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
21. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
22. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
23. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
24. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
25. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
26. For reviews, see: (a) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. II, pp 833-884. (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1. (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (e) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1993. For selected examples, see: (f) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (g) Matt, P. V., Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (h) Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508.
27. For examples of reaction systems using cyclic substrates, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (d) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
28. For examples of reaction systems using cyclic substrates, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (d) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
29. For examples of reaction systems using cyclic substrates, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (d) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
30. For examples of reaction systems using cyclic substrates, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (d) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
31. Ding, K.; Zhao, D. Chinese Patent pending (01126762.6; 03115826.9).
32. For recent examples of polymer-supported catalysts for asymmetric allylation, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Song, C. E.; Yang, J. W.; Roh, E. J.; Lee, S.-G.; Ahn, J. H.; Han, H. Angew. Chem., Int. Ed. 2002, 41, 3852. (c) Trost, B. M.; Pan, Z.; Zambrano, J.; Kujat, C. Angew. Chem., Int. Ed. 2002, 41, 4691.
33. For recent examples of polymer-supported catalysts for asymmetric allylation, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Song, C. E.; Yang, J. W.; Roh, E. J.; Lee, S.-G.; Ahn, J. H.; Han, H. Angew. Chem., Int. Ed. 2002, 41, 3852. (c) Trost, B. M.; Pan, Z.; Zambrano, J.; Kujat, C. Angew. Chem., Int. Ed. 2002, 41, 4691.
34. For recent examples of polymer-supported catalysts for asymmetric allylation, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Song, C. E.; Yang, J. W.; Roh, E. J.; Lee, S.-G.; Ahn, J. H.; Han, H. Angew. Chem., Int. Ed. 2002, 41, 3852. (c) Trost, B. M.; Pan, Z.; Zambrano, J.; Kujat, C. Angew. Chem., Int. Ed. 2002, 41, 4691.