C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions

Tetrahedron Letters

Volumn 50, Issue 52, 2009, Pages 7388-7391

  Ma, Yuanhui ^a   Zhang, Yong Jian ^a   Jin, Shangbin ^a   Li, Qiqi ^a   Li, Chenguang ^a   Lee, Junseong ^b   Zhang, Wanbin ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

Bipyrrolidines; C2 Symmetry; Diels Alder reaction; Organocatalyst

Indexed keywords

ALDEHYDE; IMINE; PYRROLIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

ALNUS;

EID: 70449133493     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.067     Document Type: Article

References (46)

1. For recent reviews on asymmetric organocatalysis, see:. Berkessel A., and Groger H. Asymmetric Organocatalysis: From Biomemetic Concepts to Applications in Asymmetric Synthesis (2005), Wiley-VCH, Weinheim
2. Dalko P.I. Enantioselective Organocatalysis (2007), Wiley-VCH, Weinheim
3. List B., and Yang J.W. Science 313 (2006) 1584
4. MacMillan D.W.C. Nature 455 (2008) 304
5. Dondoni A., and Massi A. Angew. Chem., Int. Ed. 47 (2008) 463
6. Hajos Z.G., and Parrish D.R. J. Org. Chem. 39 (1974) 1615
7. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395
8. List B. J. Am. Chem. Soc. 122 (2000) 9336
9. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260
10. List B., Pojarliev P., and Martin H.J. Org. Lett. 3 (2001) 2423
11. For recent reviews, see:. Mukherjee S., Yang J.W., Hoffmann S., and List B. Chem. Rev. 107 (2007) 5471
12. Erkkilä A., Majander I., and Pihko P.M. Chem. Rev. 107 (2007) 5416
13. Alexakis A., Tomassini A., Chouillet C., Roland S., Mangeney P., and Bernardinelli G. Angew. Chem., Int. Ed. 39 (2000) 4093
14. N-i-Pr-2,2′-Bipyrrolidine was successfully used in asymmetric Michael addition, see:. Sulzer-Mosse S., Tissot M., and Alexakis A. Org. Lett. 9 (2007) 3749
15. Mosse S., and Alexakis A. Org. Lett. 7 (2005) 4361
16. Andrey O., Alexakis A., Tomassini A., and Bernardinelli G. Adv. Synth. Catal. 346 (2004) 1147
17. Andrey O., Alexakis A., and Bernardinelli G. Org. Lett. 5 (2003) 2559
18. Alexakis A., and Andrey O. Org. Lett. 4 (2002) 3611
19. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York
20. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis I-III (1999), Springer, Berlin
21. Maruoka K., Ooi T., and Kano T. Chem. Commun. (2007) 1487 and references cited therein
22. Uyeda C., and Jacobsen E.N. J. Am. Chem. Soc. 130 (2008) 9228
23. Wen Y., Xiong Y., Chang L., Huang J., Liu X., and Feng X. J. Org. Chem. 72 (2007) 7715
24. Kim H., Yen C., Preston P., and Chin J. Org. Lett. 8 (2006) 5239
25. Kano T., Tanaka Y., and Maruoka K. Org. Lett. 8 (2006) 2687
26. Kano T., Tanaka Y., and Maruoka K. Chem. Asian J. 2 (2007) 1161
27. Sakakura A., Suzuki K., Nakano K., and Ishihara K. Org. Lett. 8 (2006) 2229
28. Marigo M., Bachmann S., Halland N., Braunton A., and Jørgensen K.A. Angew. Chem., Int. Ed. 43 (2004) 5507
29. For recent reviews of enantioselective Diels-Alder reactions, see:. Evans D.A., and Johnson J.S. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 3 (1999), Springer, New York 1177
30. Corey E.J. Angew. Chem., Int. Ed. 41 (2002) 1650
31. Nicolaou K.C., Snyder S.A., Montagnon T., and Vassilikogiannakis G. Angew. Chem., Int. Ed. 41 (2002) 1668
32. Hayashi Y. In: Kobayashi S., and Jørgensen K.A. (Eds). Cycloaddition Reactions in Organic Synthesis (2002), Wiley-VCH, Weinheim Chapter 1
33. Ahrendt K.A., Borths C.J., and Macmillan D.W.C. J. Am. Chem. Soc. 122 (2000) 4243
34. Northrup A.B., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 2458
35. Lemay M., and Ogilvie W.W. Org. Lett. 7 (2005) 4141
36. Ishihara K., and Nakano K. J. Am. Chem. Soc. 127 (2005) 10504
37. Bonini B.F., Capitò E., Comes-Franchini M., Fochi M., Ricci A., and Zwanenburg B. Tetrahedron: Asymmetry 17 (2006) 3135
38. Langlois Y., Petit A., Rémy P., Scherrmann M.-C., and Kouklovsky C. Tetrahedron Lett. 49 (2008) 5576
39. Gotoh H., and Hayashi Y. Org. Lett. 9 (2007) 2859
40. Hayashi Y., Samanta S., Gotoh H., and Ishikawa H. Angew. Chem., Int. Ed. 47 (2008) 6634
41. He H., Pei B.-J., Chou H.-H., Tian T., Chan W.-H., and Lee A.W.M. Org. Lett. 10 (2008) 2421
42. Kim K.H., Lee S., Lee D.-W., Ko D.-H., and Ha D.-C. Tetrahedron Lett. 46 (2005) 5991
43. Biaggi C., Benaglia M., Rossi S., Proto S., and Annunziata R. Tetrahedron Lett. 48 (2007) 8521
44. Ishihara K., Nakano K., and Akakura M. Org. Lett. 10 (2008) 2893
45. Refs. 7e-g.
46. Fiorelli C., Maini L., Martelli G., Savoia D., and Zazzetta C. Tetrahedron 58 (2002) 8679