Highly enantioselective ene-type spiro-cyclization of allyl propargyl ethers catalyzed by cationic palladium(II) complexes with a new type of PN-ligand bearing achiral gem-dimethyl oxazoline

Journal of Molecular Catalysis A: Chemical

Volumn 196, Issue 1-2, 2003, Pages 165-169

  Hatano, Manabu ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric catalysis; Cyclizations; Enynes; Palladium; PN ligands; Spiro

Indexed keywords

CATALYSIS; PALLADIUM; POSITIVE IONS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

ETHERS;

ALLYL COMPOUND; ETHER DERIVATIVE; LIGAND; METAL COMPLEX; OXAZOLINE DERIVATIVE; PALLADIUM COMPLEX; SPIRO COMPOUND;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037381415     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(02)00647-7     Document Type: Article

References (31)

1. S.F. Martin, Tetrahedron 36 (1980) 419-460.
2. K. Fuji, Chem. Rev. 93 (1993) 2037-2066.
3. A. Ashimori, L.E. Overman, J. Org. Chem. 57 (1992) 4571-4572.
4. L.E. Overman, D.J. Poon, Angew. Chem. Int. Ed. Engl. 36 (1997) 518-521.
5. L. Ripa, A. Hallberg, J. Org. Chem. 62 (1997) 595-602.
6. A. Ashimori, B. Bachand, L.E. Overman, D.J. Poon, J. Am. Chem. Soc. 120 (1998) 6477-6487.
7. E. Negishi, C. Coperet, S. Ma, S.Y. Liou, F. Liu, Chem. Rev. 96 (1996) 365-393.
8. B.M. Trost, M. Lautens, J. Am. Chem. Soc. 107 (1985) 1781-1783.
9. B.M. Trost, M.J. Krische, Synlett (1998) 1-16.
10. B.M. Trost, Acc. Chem. Res. 23 (1990) 34-42.
11. B.M. Trost, Chem. Eur. J. 4 (1998) 2405-2412.
12. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 102 (2002) 813-834.
13. B.M. Trost, D.C. Lee, F. Rise, Tetrahedron Lett. 30 (1989) 651-654.
14. B.M. Trost, B.A. Czeskis, Tetrahedron Lett. 35 (1994) 211-214.
15. A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. Int. Ed. Engl. 35 (1996) 662-663.
16. P. Cao, X. Zhang, Angew. Chem. Int. Ed. Engl. 39 (2000) 4104-4106.
17. A. Lei, M. He, X. Zhang, J. Am. Chem. Soc. 124 (2002) 8198-8199.
18. Q. Zhang, X. Lu, J. Am. Chem. Soc. 122 (2000) 7604-7605.
19. Q. Zhang, X. Lu, X. Han, J. Org. Chem. 66 (2001) 7676- 7684.
20. M. Hatano, M. Terada, K. Mikami, Angew. Chem. Int. Ed. Engl. 40 (2001) 249-253.
21. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumibayashi, Adv. Synth. Catal. 343 (2001) 264-267; EP 850945A (1998), US 5872273 (1999).
22. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumibayashi, Adv. Synth. Catal. 343 (2001) 264-267; EP 850945A (1998), US 5872273 (1999).
23. M. Hatano, K. Mikami, Angew. Chem. Int. Ed. Engl., submitted for publication.
24. M. Ogasawara, K. Yoshida, H. Kamei, K. Kato, Y. Uozumi, T. Hayashi, Tetrahedron Asymm. 9 (1998) 1779-1787.
25. M. Ogasawara, K. Yoshida, T. Hayashi, Heterocycles 52 (2000) 195-201.
26. Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda, Tetrahedron Lett. 39 (1998) 4343-4346.
27. K. Selvakumar, M. Valentini, M. Wörle, P.S. Pregosin, A. Albinati, Organometallics 18 (1999) 1207-1215.
28. K. Selvakumar, M. Valentini, P.S. Pregosin, A. Albinati, F. Eisenträger, Organometallics 19 (2000) 1299-1307.
29. P. Dotta, A. Magistrate, U. Rothlisberger, P.S. Pregosin, A. Albinati, Organometallics 21 (2002) 3033-3041.
30. O. Loiseleur, P. Meier, A. Pfaltz, Angew. Chem. 108 (1996) 218-220.
31. O. Loiseleur, P. Meier, A. Pfaltz, Angew. Chem. Ind. Ed. Engl. 35 (1996) 200-201.