Convenient synthesis of pyrrolidines by amphiphilic allylation of imines with 2-methylenepropane-1,3-diols

Angewandte Chemie - International Edition

Volumn 47, Issue 31, 2008, Pages 5803-5805

  Kimura, Masanari ^a   Tamaki, Takato ^a   Nakata, Masanori ^a   Tohyama, Katsumi ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Aldimines; Allylation; Amphiphiles; Palladium; Pyrrolidines

Indexed keywords

ALDIMINES; ALLYLATION; AMPHIPHILES; PYRROLIDINES;

ALDEHYDES; AMINES; CHEMICAL REACTIONS; COMPLEXATION; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PALLADIUM;

SYNTHESIS (CHEMICAL);

ALLYL ALCOHOL; DRUG DERIVATIVE; IMINE; PROPANE; PROPANOL; PYRROLIDINE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

IMINES; PROPANE; PROPANOLS; PYRROLIDINES;

EID: 53549085445     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801252     Document Type: Article

References (30)

1. a) "Cycloaddition Reactions of Allylpalladium and Related Derivatives": S. Ogoshi in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2 (Ed.: E. Negishi), Wiley Interscience, New York, 2002, pp. 1995-2009;
2. b) S. Yamago, E. Nakamura, Organic Reactions, Vol. 61 (Ed.: L. E. Overman), Wiley, New York, 2002, pp. 1-217;
3. c) B. M. Trost, N. Cramer, H. Bernsmann, J. Am. Chem. Soc. 2007, 129, 3086-3087;
4. d) S. Xu, H. Arimoto, D. Uemura, Angew. Chem. 2007, 119, 5848-5851;
5. Angew. Chem. Int. Ed. 2007, 46, 5746-5749.
6. a) B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1979, 101, 6429-6432;
7. b) B. M. Trost, N. Cramer, S. M. Silverman, J. Am. Chem. Soc. 2007, 129, 12396-12397;
8. c) B. M. Trost, S. M. Silverman, J. P. Stambuli, J. Am. Chem. Soc. 2007, 129, 12398-12399;
9. d) for [3+3] cycloaddition of TMM-Pd with azomethine imines, see: R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 6330-6331;
10. e) for asymmetric [3+3] cycloaddition of TMM-Pd with nitrones, see: R. Shintani, S. Park, W.-L. Duan, T. Hayashi, Angew. Chem. 2007, 119, 6005-6007;
11. Angew. Chem. Int. Ed. 2007, 46, 5901-5903.
12. a) Y. Tamaru, Y. Horino, M. Araki, S. Tanaka, M. Kimura, Tetrahedron Lett. 2000, 41, 5705-5709;
13. b) Y. Horino, M. Naito, M. Kimura, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 2001, 42, 3113-3116;
14. c) M. Kimura, Y. Horino, R. Mukai, S. Tanaka, Y. Tamaru, J. Am. Chem. Soc. 2001, 123, 10401-10402;
15. d) M. Kimura, R. Mukai, N. Tanigawa, S. Tanaka, Y. Tamaru, Tetrahedron 2003, 59, 7767-7777;
16. e) M. Kimura, M. Futamata, R. Mukai, Y. Tamaru, J. Am. Chem. Soc. 2005, 127, 4592-4593;
17. f) M. Kimura, M. Fukasaka, Y. Tamaru, Synthesis 2006, 3611-3616.
18. a) M. Kimura, I. Kiyama, T. Tomizawa, Y. Horino, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 1999, 40, 6795-6798;
19. b) M. Kimura, T. Tomizawa, Y. Horino, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 2000, 41, 3627-3629;
20. c) M. Kimura, M. Shimizu, K. Shibata, M. Tazoe, Y. Tamaru, Angew. Chem. 2003, 115, 3514-3517;
21. Angew. Chem. Int. Ed. 2003, 42, 3392-3395;
22. d) M. Shimizu, M. Kimura, T. Watanabe, Y. Tamaru, Org. Lett. 2005, 7, 637-640.
23. R. Mukai, Y. Horino, S. Tanaka, Y. Tamaru, M. Kimura, J. Am. Chem. Soc. 2004, 126, 11138-11139.
24. B. M. Trost, S. A. King, T. Schmidt, J. Am. Chem. Soc. 1989, 111, 5902-5915.
25. 3B, the conversion decreased to 50%.
26. a) M. Kimura, A. Miyachi, K. Kojima, S. Tanaka, Y. Tamaru, J. Am. Chem. Soc. 2004, 126, 14360-14361;
27. b) M. Kimura, Y. Tatsuyama, K. Kojima, Y. Tamaru, Org. Lett. 2007, 9, 1871-1873.
28. w) = 0.1071-(0.1254). CCDC 671566 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
29. B. M. Trost, C. M. Marrs, J. Am. Chem. Soc. 1993, 115, 6636-6645.
30. 2Zn at 50°C for 72 h.