Asymmetric Organocatalytic Diels-Alder Reactions on Solid Support

Advanced Synthesis and Catalysis

Volumn 344, Issue 9, 2002, Pages 941-945

  Selkälä, Sami A ^a   Tois, Jan ^a   Pihko, Petri M ^a   Koskinen, Ari M P ^a  

^a AALTO UNIVERSITY   (Finland)

Author keywords

Asymmetric catalysis; Cycloaddition; Organocatalysis; Solid phase catalysis

Indexed keywords

EID: 0344613309     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200210)344:9<941::AID-ADSC941>3.0.CO;2-M     Document Type: Article

References (35)

1. For recent reviews on organocatalytic reactions, see: a) P. I. Dalko, L. Moisan, Angew. Chem., Int. Ed. 2001, 40, 3726; Angew. Chem. 2001, 113, 3840; b) B. List, Synlett 2001, 1675; for a review of peptides and peptidomimetics as organocatalysts, see: c) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481.
2. For recent reviews on organocatalytic reactions, see: a) P. I. Dalko, L. Moisan, Angew. Chem., Int. Ed. 2001, 40, 3726; Angew. Chem. 2001, 113, 3840; b) B. List, Synlett 2001, 1675; for a review of peptides and peptidomimetics as organocatalysts, see: c) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481.
3. For recent reviews on organocatalytic reactions, see: a) P. I. Dalko, L. Moisan, Angew. Chem., Int. Ed. 2001, 40, 3726; Angew. Chem. 2001, 113, 3840; b) B. List, Synlett 2001, 1675; for a review of peptides and peptidomimetics as organocatalysts, see: c) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481.
4. For recent reviews on organocatalytic reactions, see: a) P. I. Dalko, L. Moisan, Angew. Chem., Int. Ed. 2001, 40, 3726; Angew. Chem. 2001, 113, 3840; b) B. List, Synlett 2001, 1675; for a review of peptides and peptidomimetics as organocatalysts, see: c) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481.
5. a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem., Int. Ed. Engl. 1971, 10, 496;
6. b) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615;
7. c) H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417.
8. a) B. List, R. A. Lerner, C. F. Barbas, III, J. Am. Chem. Soc. 2000, 122, 2395;
9. b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, III, J. Am. Chem. Soc. 2001, 725, 5260;
10. c) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas, III, Tetrahedron Lett. 2001, 42, 4441;
11. d) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas, III, Tetrahedron Lett. 2002, 43, 3817;
12. e) B. List, J. Am. Chem. Soc. 2002 124, 5656;
13. f) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem., Int. Ed. 2002, 41, 1790; Angew. Chem. 2002, 114, 1868.
14. f) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem., Int. Ed. 2002, 41, 1790; Angew. Chem. 2002, 114, 1868.
15. a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
16. b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
17. c) W. S. Jen, J. J. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874;
18. d) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370;
19. e) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172.
20. Independently from us, the Cozzi group recently disclosed a homogeneous polymer-supported imidazolidinone catalyst for the enantioselective Diels-Alder reaction: M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149.
21. For recent reviews of enantioselective Diels-Alder reactions and their applications in total synthesis, see: a) E. J. Corey, Angew. Chem., Int. Ed. 2002, 41, 1650; Angew. Chem. 2002, 114, 1724; b) K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem., Int. Ed. 2002, 41, 1668; Angew. Chem. 2002, 114, 1742; b) Y. Hayashi, in Cycloaddition Reactions in Organic Synthesis, (Eds.: S. Kobayashi, K. A. Jorgensen), Wiley-VCH, Weinheim, 2001, pp. 5-56.
22. For recent reviews of enantioselective Diels-Alder reactions and their applications in total synthesis, see: a) E. J. Corey, Angew. Chem., Int. Ed. 2002, 41, 1650; Angew. Chem. 2002, 114, 1724; b) K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem., Int. Ed. 2002, 41, 1668; Angew. Chem. 2002, 114, 1742; b) Y. Hayashi, in Cycloaddition Reactions in Organic Synthesis, (Eds.: S. Kobayashi, K. A. Jorgensen), Wiley-VCH, Weinheim, 2001, pp. 5-56.
23. For recent reviews of enantioselective Diels-Alder reactions and their applications in total synthesis, see: a) E. J. Corey, Angew. Chem., Int. Ed. 2002, 41, 1650; Angew. Chem. 2002, 114, 1724; b) K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem., Int. Ed. 2002, 41, 1668; Angew. Chem. 2002, 114, 1742; b) Y. Hayashi, in Cycloaddition Reactions in Organic Synthesis, (Eds.: S. Kobayashi, K. A. Jorgensen), Wiley-VCH, Weinheim, 2001, pp. 5-56.
24. For recent reviews of enantioselective Diels-Alder reactions and their applications in total synthesis, see: a) E. J. Corey, Angew. Chem., Int. Ed. 2002, 41, 1650; Angew. Chem. 2002, 114, 1724; b) K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem., Int. Ed. 2002, 41, 1668; Angew. Chem. 2002, 114, 1742; b) Y. Hayashi, in Cycloaddition Reactions in Organic Synthesis, (Eds.: S. Kobayashi, K. A. Jorgensen), Wiley-VCH, Weinheim, 2001, pp. 5-56.
25. For recent reviews of enantioselective Diels-Alder reactions and their applications in total synthesis, see: a) E. J. Corey, Angew. Chem., Int. Ed. 2002, 41, 1650; Angew. Chem. 2002, 114, 1724; b) K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem., Int. Ed. 2002, 41, 1668; Angew. Chem. 2002, 114, 1742; b) Y. Hayashi, in Cycloaddition Reactions in Organic Synthesis, (Eds.: S. Kobayashi, K. A. Jorgensen), Wiley-VCH, Weinheim, 2001, pp. 5-56.
26. Available from Aldrich. See also: P. H. Toy, K. D. Janda, Tetrahedron Lett. 1999, 40, 6329.
27. [8b] tests to detect the presence of primary and secondary free amines, respectively, for the purposes of monitoring the reactions on solid support. See: a) E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595 (Kaiser test); b) T. Vojkovsky, Pept. Res. 1995, 8, 236 (chloranil test).
28. [8b] tests to detect the presence of primary and secondary free amines, respectively, for the purposes of monitoring the reactions on solid support. See: a) E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595 (Kaiser test); b) T. Vojkovsky, Pept. Res. 1995, 8, 236 (chloranil test).
29. J. D. Fontenot, J. M. Ball, J. M. Miller, C. M. David, R. C. Montelaro, Pept. Res. 1991, 4, 19.
30. K. Ishihara, K. Kurihara, M. Matsumoto, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 6920.
31. For examples of a silica-supported organocatalyst, see: K.-i. Shimizu, H. Suzuki, E. Hayashi, T. Kodama, Y. Tsuchiya, H. Hagiwara, Y. Kitayama, Chem. Commun. 2002, 1068 and references cited therein.
32. The n-propylamine loading was 0.53 mmol/g in the silica gel used.
33. L. A. Carpino, B. J. Cohen, K. E. Stephens, Jr, S. Y. Sadat-Aalaee, J.-H. Tien, D. C. Langridge, J. Org. Chem. 1986, 51, 3732; M. Beyermann, M. Bienert, H. Niedrich, J. Org. Chem. 1986, 57, 721.
34. L. A. Carpino, B. J. Cohen, K. E. Stephens, Jr, S. Y. Sadat-Aalaee, J.-H. Tien, D. C. Langridge, J. Org. Chem. 1986, 51, 3732; M. Beyermann, M. Bienert, H. Niedrich, J. Org. Chem. 1986, 57, 721.
35. MeOH was also used successfully as the solvent with the catalyst 5. In this case, however, the product aldehydes were converted into their corresponding dimethyl acetals.