Solvent-enhanced diastereo- and regioselectivity in the pd IIcatalyzed synthesis of six- and eight-membered heterocycles via cis-aminopalladation

Chemistry - A European Journal

Volumn 15, Issue 30, 2009, Pages 7376-7381

  Balázs, Árpád ^a   Hetényi, Anasztázia ^a   Szakonyi, Zsolt ^a   Sillanpää, Reijo ^c   Fülöp, Ferenc ^a,b  

^a UNIVERSITY OF SZEGED   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Allylic compounds; Amirtation; Domino reactions; Oxidation; Palladium

Indexed keywords

ALLYLIC COMPOUNDS; AMINATION REACTION; AMIRTATION; CATALYZED SYNTHESIS; DIASTEREO-SELECTIVITY; DOMINO REACTIONS; EFFICIENT SYNTHESIS; HETEROCYCLES; OXIDATIVE CYCLIZATION; PYRIMIDIN-4-ONES; SOLVENT EFFECTS;

AMINES; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

PALLADIUM;

2 AMINOCYCLOHEXANECARBOXYLIC ACID; 2-AMINOCYCLOHEXANECARBOXYLIC ACID; ALLYL COMPOUND; AZOCINE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; CYCLOHEXYLAMINE DERIVATIVE; PALLADIUM; PYRIMIDINONE DERIVATIVE; VINYL DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; AMINATION; AZOCINES; CATALYSIS; CYCLIZATION; CYCLOHEXANECARBOXYLIC ACIDS; CYCLOHEXANES; CYCLOHEXYLAMINES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; PYRIMIDINONES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 67651064661     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900477     Document Type: Article

References (44)

1. a) J. Tsuji, Palladium Reagents and Catalysts, Wiley, New York, 2004;
2. b) E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley, New York. 2002;
3. c) R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584-3585;
4. d) S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501;
5. Angew. Chem. Int. Ed. 2004, 43, 3400-3420;
6. e) S. S. Stahl, Science 2005, 309, 1824-1826;
7. f) E. J. Alexanian, C Lee, E. J. Sorensen, J. Am. Chem. Soc. 2005, 127, 7690-7691;
8. g) J. Streuff, C. H. Hövelmann, M. Nieger, K. Muñiz, J. Am. Chem. Soc. 2005, 127, 14586-14587;
9. h) M. M. Rogers, J. E. Wendland, I. A. Guzei. S. S. Stahl, Org. Lett. 2006, 8, 2257-2260;
10. i) K.-T. Yip, M. Yang, K.-L. Law. N.Y. Zhu, D. Yang, J. Am. Chem. Soc. 2006, 128, 3130-3131;
11. j) V. Kolov. C. C. Scarborough, S. S. Stahl, Inorg. Chem. 2007, 46, 1910-1923:
12. k) G. Liu, S. S. Stahl. J. Am. Chem. Soc. 2007, 129, 6328-6335;
13. l) A. Minatti, K. Muñiz, Chem. Soc. Rev. 2007, 36, 1142-1152;
14. m) E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318-5365:
15. n) Z. Zhang, J. Zhang. J. Tan. Z. Wang. J. Org. Chem. 2008, 73, 5180-5182;
16. o) Z. Zhang, J. Tan. Z. Wang. Org. Lett. 2008, 10, 173-175.
17. S. L. Schreiber, Science 2000, 287, 1964-1969.
18. a) T. Shinohara, M. A. Arai, K. Wakita, T Arai, H. Sasai, Tetrahedron Lett. 2003, 44, 711-714;
19. b) R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. M. Stoltz. Angew. Chem. 2003, 115, 2998-3001;
20. Angew. Chem. Int. Ed. 2003, 42, 2892-2895;
21. c) L. F. Tietze, H. Ha, H. P. Bell, Chem. Rev. 2004, 104, 3453-3516;
22. d) R. M. Trend, Y. K. Ramtohul, B. M. Stoltz, J. Am. Chem. Soc. 2005, 127, 17778-17788;
23. e) S. F. Kirsch. L. E. Overman, J. Org. Chem. 2005, 70, 2859-2861.
24. E. M. Beccalli, G. Broggini, G. Paladino, A. Penoni, C Zoni. J. Org. Chem. 2004, 69, 5627-5630.
25. F. Fülöp, T. A. Martinek, G. K. Tóth, Chem. Soc. Rev. 2006, 35, 323-334.
26. a) E. Beccalli, G. Broggini, M. Martinelli, G. Palladino, Synlett 2006, 73-76;
27. b) J. Muzart, Tetrahedron 2005, 61, 4179-4212.
28. a) S. Bienz, P. Bisegger, A. Guggisberg, M. Hesse, Nat. Prod. Rep. 2005, 22, 647-658;
29. b) B. Rasmussen, A.-J. Nkurunziza, M. Witt, H. A. Oketch-Rabah, J. W. Jaroszewski, D. Stasrk. J. Nat. Prod. 2006, 69, 1300-1304.
30. K. A. Oppong. C D. Ellis, M. C Laufersweiler, S. V. O'Neil, Y. Wang, D. L. Soper, M. W. Baize. J. A. Wos, B. De, G. K. Bosch, A. N. Fancher. W. Lu, M. K. Suchanek, R. L. Wang, T. P. De- muth, Jr., Bioorg. Med. Chem. Lett. 2005, 15, 4291 -4294.
31. II-catalyzed transformation where the ring-closure product could be formed only via a π-allyl-palladium intermediate, but isolated the title compound in <5% yield. They therefore rejected this mechanism. In our case, we suggest that the amide moiety plays a key role in stabilizing the iso-merized product through a cross-conjugated π-system.
32. II- mediated transformations:
33. a) E. Thiery, C. Chevrin, J. Le Bras. D. Harakat, J. Muzart, J. Org. Chem. 2007, 72, 1859-1862:
34. b) M. J. Schultz. M. S. Sigman, J. Am. Chem. Soc. 2006, 128, 1460-1461.
35. J. A. Keith, R. J. Nielsen, J. Oxgaard. W. A. Goddard III. J. Am. Chem. Soc. 2007, 129, 12342-12343.
36. J. M. Keith, W. A. Goddard III, J. Oxgaard, J. Am. Chem. Soc. 2007, 129, 10361-10369.
37. a) B. V. Popp, S. S. Stahl, J. Am. Chem. Soc. 2007, 129, 4410-4422;
38. b) B. V. Popp, J. E. Wendlandt, C. R. Landis, S. S. Stahl, Angew. Chem. 2007, 119, 607-610;
39. Angew. Chem. Int. Ed. 2007, 46, 601-604.
40. a) T. Hosokawa. S.-I. Murahashi, Acc. Client. Res. 1990, 23, 49-54:
41. b) T. Nishimura, N. Kakiuchi, T. Onoue, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 1915-1918.
42. M. Kimura, H. Harayama, S. Tanaka, Y. Tamaru, J. Chem. Soc. Chem. Commun. 1994, 2531.
43. J. Piera, A. Persson, X. Caldentey, J.-E. Bäckvall, J. Am. Chem. Soc. 2007, 129, 14120-14121.
44. In the presence of benzoquinone as catalyst oxidant, no cyclization took place and only unreacted starting material was isolated from the mixture.