Highly enantioselective Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13400-13401

  Longmire, James M ^a   Wang, Bin ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; COBALT; EPHEDRINE; ESTER; FERROCENE DERIVATIVE; METAL; SILVER;

ARTICLE; CATALYSIS; CHIRALITY; CYCLOADDITION; STOICHIOMETRY;

AZO COMPOUNDS; CATALYSIS; CYCLIZATION; MALEATES; PYRROLIDINES; SILVER; STEREOISOMERISM;

EID: 0037073234     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja025969x     Document Type: Article

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45. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
46. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
47. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
48. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
49. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
50. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
51. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Torium, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. (c) Jiang, Q,; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100. (d) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799. (e) Trost, B. M.; Van Vranken, D. L,; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (f) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435. Ligand 6a has been independently prepared in Dai and Hou's groups: (g) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Gao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.