Platinum-catalyzed diastereoselective intramolecular coupling of allyl halides and hydrazones

Journal of Organic Chemistry

Volumn 76, Issue 16, 2011, Pages 6877-6882

  Hong, Jong Tai ^a   Jang, Hye Young ^a  

^a Ajou University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL HALIDES; CIS-SELECTIVITY; CYCLIC AMINES; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; GOOD YIELD; HYDRAZONES; INTRAMOLECULAR COUPLING; PLATINUM COMPLEXES; PLATINUM SPECIES;

CATALYSIS; COMPLEXATION; PLATINUM; STEREOSELECTIVITY;

PLATINUM COMPOUNDS;

ALLYL COMPOUND; HALIDE; HYDRAZONE DERIVATIVE; HYDROGEN; PLATINUM; TIN CHLORIDE;

ADDITION REACTION; ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CYCLIZATION; DIASTEREOISOMER;

EID: 80051720859     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200993v     Document Type: Article

References (31)

1. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293
2. Zanoni, G.; Pontiroli, A.; Marchetti, A.; Vidari, G. Eur. J. Org. Chem. 2007, 3599-3611
3. Estévez, R. E.; Justicia, J.; Bazdi, B.; Fuentes, N.; Paradas, M.; Choquesillo-Lazarte, D.; García-Ruiz, J. M.; Robles, R.; Gansäuer, A.; Cuerva, J. M.; Oltra, J. E. Chem. Eur. J. 2009, 15, 2774-2791
4. Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140-1141
5. Lee, J.-Y.; Miller, J. J.; Hanilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837-1839
6. Miller, J. J.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 2752-2753 and references cited therein
7. Tang, L.; Ding, L.; Chang, W.-X.; Li, J. Tetrahedron Lett. 2006, 47, 303-306
8. Zhao, X.-L.; Liu, L.; Chen, Y.-J.; Wang, D. Tetrahedron 2006, 62, 7113-7120
9. Masuyam, Y.; Marukawa, M. Tetrahedron Lett. 2007, 48, 5963-5965 and references cited therein
10. Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958-2963
11. Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6745-6751
12. Haddad, T. D.; Hirayama, L. C.; Singaram, B. J. Org. Chem. 2010, 75, 642-649 and references cited therein
13. Park, J.-Y.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4901-4908
14. Sebelius, S.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2003, 5, 3065-3068
15. Li, C.-J. Chem. Rev. 2005, 105, 3095-3165
16. Kim, S. J.; Jang, D. O. J. Am. Chem. Soc. 2010, 132, 12168-12169
17. Lu, Y.; Kim, I. S.; Hassan, A.; Del Valle, D. J.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 5018-5021
18. Zhang, Y. J.; Yang, J. H.; Kim, S. H.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 4562-4563
19. Han, S. B.; Gao, X.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 9153-9156 and references cited therein
20. Yu, C.-M.; Lee, S.; Hong, Y.-T.; Yoon, S.-K. Tetrahedron Lett. 2004, 45, 6557-6561
21. Denmark, S. E.; Nguyen, S. T. Org. Lett. 2009, 11, 781-784
22. Hong, J.-T.; Wang, X.; Kim, J.-H.; Kim, K.; Yun, H.; Jang, H.-Y. Adv. Synth. Catal. 2010, 352, 2949-2954
23. Kim, S.-H.; Oh, S.-J.; Yu, C.-M. Chem. Commun. 2007, 5025-5027
24. Ruegg, H. J.; Pregosin, P. S. J. Organomet. Chem. 1986, 316, 233-241
25. Shinde, M. P.; Wang, X.; Kang, E. J.; Jang, H.-Y. Eur. J. Org. Chem. 2009, 6091-6094
26. Jang, M.-S.; Wang, X.; Jang, W.-Y.; Jang, H.-Y. Organometallics 2009, 28, 4841-4844
27. Williams, B. S.; Holland, A. W.; Goldberg, K. I. J. Am. Chem. Soc. 1999, 121, 252-253
28. van der Boom, M. E.; Kraatz, H.-B.; Hassner, L.; Ben-David, Y.; Milstein, D. Organometallics 1999, 18, 3873-3884
29. Fekl, U.; Kaminsky, W.; Goldberg, K. I. J. Am. Chem. Soc. 2001, 123, 6423-6424
30. For the reaction of nucleophilic allylic platinum intermediates, see: Suginome, M.; Nakamura, H.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 1998, 120, 4248-4249
31. For the oxidative addition of acids to platinum(II) species, see: Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Inorg. Chem. 1998, 37, 2422-2431