[4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst

Journal of the American Chemical Society

Volumn 131, Issue 36, 2009, Pages 12904-12905

  Ueno, Satoshi ^a   Ohtsubo, Masakazu ^a   Kuwano, Ryoichi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; BENZYLIC; CATALYTIC REACTIONS; CHEMICAL EQUATIONS; HETERO-DIELS-ALDER REACTIONS; HIGH YIELD; PALLADIUM CATALYST; TETRAHYDROISOQUINOLINES;

CATALYSIS; NITROGEN COMPOUNDS; PALLADIUM; REACTION RATES; SILANES;

CATALYSTS;

2 XYLYLENE DERIVATIVE; ALKENE; ALKYNE; IMINE; PALLADIUM; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; XYLENE;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLOADDITION; DIELS ALDER REACTION; REACTION ANALYSIS;

EID: 70349112713     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905988e     Document Type: Article

References (25)

1. Reviews:(a) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
2. (b) Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199-3246.
3. Reviews: (a) Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099-6138.
4. (b) Heintzelman, G. R.; Meigh, I. R.; Mahajan, Y. R.; Weinreb, S. M. Org. React. 2005, 65, 141-599.
5. (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1972, 11, 1031-1032.
6. (b) Kametani, T.; Takahashi, T.; Ogasawara, K.; Fukumoto, K. Tetrahedron 1974, 30, 1047-1051.
7. (c) Berkowitz, W. F.; John, T. V. J. Org. Chem. 1984, 49, 5269-5271.
8. (d) Craig, D.; Robson, M. J.; Shaw, S. J. Synlett 1998, 1381-1383.
9. (e) Hentemann, M. F.; Allen, J. G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 1937-1940.
10. Kuwano, R.; Shige, T. J. Am. Chem. Soc. 2007, 129, 3802-3803.
11. DPPPent = 1,5-bis(diphenylphosphino)pentane: Sacconi, L.; Gelsomini, J. Inorg. Chem. 1968, 7, 291-294.
12. DPPPent ligand is effective for the Suzuki-Miyaura coupling of benzylic carbonates: Kuwano, R.; Yokogi, M. Org. Lett. 2005, 7, 945-947.
13. (a) Tamao, K.; Yoshida, J.; Takahashi, M.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Kurita, A.; Kumada, M. J. Am. Chem. Soc. 1978, 100, 290-292.
14. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542-549.
15. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 18, 1711-1714.
16. (a) Beard, A. R.; Hazell, S. J.; Mann, J.; Palmer, C. J. Chem. Soc., Perkin Trans. 1 1993, 1235-1238.
17. (b) Fleming, I.; Morgan, I. T.; Sarkar, A. K. J. Chem. Soc., Perkin Trans. 1 1998, 2749-12746
18. Kuwano, R.; Shige, T. Chem. Lett. 2005, 34, 728-729.
19. Yoshida et al. used 1 as an o-xylylene precursor in the distannylation and disilylation of o-xylylenes with a palladium catalyst and potassium fluoride: (a) Yoshida, H.; Nakano, S.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Org. Lett. 2006, 8, 4157-4159.
20. (b) Yoshida, H.; Nakano, S.; Mukae, M.; Ohshita, J. Org. Lett. 2008, 10, 4319-4322.
21. 1H NMR analysis of the resulting mixture. See details in the Supporting Information.
22. (a) Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104-12105.
23. (b) Kuwano, R. Synthesis 2009, 1049-1061.
24. Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2694-2695.
25. We attempted to use a chiral bisphosphine, Taniaphos, in place of DPPPent for the [4+2] cycloaddition of 1a with 2a under condition B. However, the product 3a was obtained in only 28% yield with 7% ee.