Challenge toward structural complexity using asymmetric catalysis: Target-oriented development of catalytic enantioselective Diels-Alder reaction

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4387-4390

  Usuda, Hiroyuki ^a   Kuramochi, Akiyoshi ^a   Kanai, Motomu ^a,b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GARSUBELLIN A; HYPERFORIN; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 9444297818     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048018s     Document Type: Article

References (35)

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17. For recent reviews on catalytic asymmetric Diels-Alder reaction, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg; Vol. III, pp 1178-1235. For a recent review on the Diels-Alder reaction in total synthesis, see: (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
18. For recent reviews on catalytic asymmetric Diels-Alder reaction, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg; Vol. III, pp 1178-1235. For a recent review on the Diels-Alder reaction in total synthesis, see: (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
19. For recent reviews on catalytic asymmetric Diels-Alder reaction, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg; Vol. III, pp 1178-1235. For a recent review on the Diels-Alder reaction in total synthesis, see: (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
20. Examples of the catalytic asymmetric intermolecular Diels-Alder reaction with complex dienes: (a) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612. (b) Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120-14125. For intramolecular reactions, see: (c) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 1305. (d) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. An example of the catalytic diastereoselective Diels-Alder reaction that produces quaternary stereocenters on a cyclohexane structure: (e) Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403. (f) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546 (asymmetric version using a stoichiometric amount of chiral auxiliary).
21. Examples of the catalytic asymmetric intermolecular Diels-Alder reaction with complex dienes: (a) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612. (b) Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120-14125. For intramolecular reactions, see: (c) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 1305. (d) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. An example of the catalytic diastereoselective Diels-Alder reaction that produces quaternary stereocenters on a cyclohexane structure: (e) Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403. (f) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546 (asymmetric version using a stoichiometric amount of chiral auxiliary).
22. Examples of the catalytic asymmetric intermolecular Diels-Alder reaction with complex dienes: (a) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612. (b) Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120-14125. For intramolecular reactions, see: (c) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 1305. (d) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. An example of the catalytic diastereoselective Diels-Alder reaction that produces quaternary stereocenters on a cyclohexane structure: (e) Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403. (f) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546 (asymmetric version using a stoichiometric amount of chiral auxiliary).
23. Examples of the catalytic asymmetric intermolecular Diels-Alder reaction with complex dienes: (a) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612. (b) Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120-14125. For intramolecular reactions, see: (c) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 1305. (d) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. An example of the catalytic diastereoselective Diels-Alder reaction that produces quaternary stereocenters on a cyclohexane structure: (e) Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403. (f) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546 (asymmetric version using a stoichiometric amount of chiral auxiliary).
24. Examples of the catalytic asymmetric intermolecular Diels-Alder reaction with complex dienes: (a) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612. (b) Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120-14125. For intramolecular reactions, see: (c) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 1305. (d) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. An example of the catalytic diastereoselective Diels-Alder reaction that produces quaternary stereocenters on a cyclohexane structure: (e) Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403. (f) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546 (asymmetric version using a stoichiometric amount of chiral auxiliary).
25. Examples of the catalytic asymmetric intermolecular Diels-Alder reaction with complex dienes: (a) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612. (b) Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120-14125. For intramolecular reactions, see: (c) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 1305. (d) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786. An example of the catalytic diastereoselective Diels-Alder reaction that produces quaternary stereocenters on a cyclohexane structure: (e) Roush, W. R.; Barda, D. A. J. Am. Chem. Soc. 1997, 119, 7402-7403. (f) Roush, W. R.; Limberakis, C.; Kunz, R. K.; Barda, D. A. Org. Lett. 2002, 4, 1543-1546 (asymmetric version using a stoichiometric amount of chiral auxiliary).
26. Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119-3154.
27. Examples of catalytic asymmetric Diels-Alder reaction using a chiral iron complex: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728-729. (b) Kündig, E. P.; Bourdin, B.; Bernardineli, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1856-1858.
28. Examples of catalytic asymmetric Diels-Alder reaction using a chiral iron complex: (a) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728-729. (b) Kündig, E. P.; Bourdin, B.; Bernardineli, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1856-1858.
29. See Supporting Information for details.
30. 3 contains crystal constitutional water, which has adverse effects on the reaction.
31. For a discussion of the importance of the π-π interaction between an asymmetric catalyst and a substrate in the catalytic enantioselective Diels-Alder reaction, see ref 7a.
32. 7a could not be used as a synthetic intermediate for 2 or 3. All attempts to introduce a side chain at the C-2 position failed due to the steric hindrance.
33. Nesper, R.; Pregosin, P.; Püntener, K.; Worle, M.; Albinati, A. J. Organomet. Chem. 1996, 507, 85-101. There was no significant difference in reactivity or enantioselectivity between Ph-pybox (4a) and 4d in the reaction of 5a and a relatively simple diene 6a: 7a was obtained in 67% yield with 90% ee under the conditions shown in Table 2. For results using other Ar-pybox ligands, see Supporting Information.
34. Use of 5 Å MS prevents undesired hydrolysis and polymerization of the diene.
35. 3N and water.