Formal Synthesis of 3-Deoxy-D-manno-2-Octulosonic Acid (KDO) via a Highly Double-Stereoselective Hetero Diels-Alder Reaction Directed by a (Salen)CoII Catalyst and Chiral Diene

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2456-2461

  Hu, Yun Jin ^a   Huang, Xiao Dong ^a   Yao, Zhu Jun ^a   Wu, Yu Lin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000865522     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971186w     Document Type: Article

References (60)

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8. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
9. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
10. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
11. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
12. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
13. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
14. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
15. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
16. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
17. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
18. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
19. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
20. For chemical synthesis see: (a) López-Herrera, P. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325. (b) Lubineau, A.; Auge J.; Lubin, N. Tetrahedron 1993, 49, 4639 and references therein, (c) Shing, K. M. Tetraheron 1992, 48, 6777 and ref 5 cited therein. Several other methods for hetero Diels-Alder reactions have also been developed. See (d) Boger, D. L.; Weinreb, S. M. Hetro Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (e) Johannsen, M.; Jørgensen K. A. J. Org. Chem. 1995, 60, 5757. (f) McGinnis, M. B.; Vagle K.; Green, J. F.; Tan, L. C.; Palmer, R.; Siler J.; Pagni, R. M.; Kabalka, G. J. Org. Chem. 1996, 61, 3496. (g) Organ, M. G.; Winkle, D. D. J. Org. Chem. 1997, 62, 1881. (h) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. (i) Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600. For reviews on the hetero Diels-Alder reactions. See: (j) Danishefsky, S. Aldrichimica Acta 1986, 19, 59. (k) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250. (l) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 273. (m) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthethsis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 661.
21. For de novo syntheses, see: (a) Martin, S. F.; Zinke, P. W. J. Org. Chem. 1991, 56, 6600. (b) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (c) Danishefsky, S. J.; DeNino, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929.
22. For de novo syntheses, see: (a) Martin, S. F.; Zinke, P. W. J. Org. Chem. 1991, 56, 6600. (b) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (c) Danishefsky, S. J.; DeNino, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929.
23. For de novo syntheses, see: (a) Martin, S. F.; Zinke, P. W. J. Org. Chem. 1991, 56, 6600. (b) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (c) Danishefsky, S. J.; DeNino, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929.
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