Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6705-6708

  Yoshida, Masahiro ^a   Ueda, Hirofumi ^b   Ihara, Masataka ^b  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Addition; Boronic acids; Oxiranes; Palladium; Propargylic compounds

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; PALLADIUM;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CROSS COUPLING REACTION; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; SYNTHESIS;

EID: 23944505184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.134     Document Type: Article

References (34)

1. For selected reviews, see: J.A. Marshall Chem. Rev. 100 2000 3163
2. R. Zimmer, C.U. Dinesh, E. Nandanan, and F.A. Khan Chem. Rev. 100 2000 3067
3. S. Ma Acc. Chem. Res. 36 2003 701
4. A.S.K. Hashmi Angew. Chem., Int. Ed. 39 2000 3590
5. A. Hoffmann-Röder, and N. Krause Angew. Chem., Int. Ed. 41 2002 2933
6. N. Krause, A. Hoffmann-Röder, and J. Canisius Synthesis 2002 1759
7. A. Hoffmann-Röder, and N. Krause Angew. Chem., Int. Ed. 43 2004 1196
8. N. Krause, and A. Hoffmann-Röder Allenic Natural Products and Pharmaceuticals N. Krause A.S.K. Hashmi Modern Allenic Chemistry 2004 Wiley-VCH Weinheim 997
9. S.R. Landor Naturally Occurring Allenes S.R. Landor The Chemistry of the Allenes 1982 Academic Press London 679
10. A. Claesson Biologically Active Allenes S.R. Landor The Chemistry of the Allenes 1982 Academic Press London 709
11. C.H. Robinson, and D.F. Covey Biological Formation and Reactions S. Patai The Chemistry of Ketenes, Allenes and Related Compounds 1980 Wiley Chichester 451
12. A. Alexakis, I. Marek, P. Mangeney, and J.F. Normant Tetrahedron 47 1991 1677
13. P. Vermeer, J. Meijer, C. De Graaf, and H. Schreures Rec. Trav. Chim. Pays-Bas 93 1974 46
14. A.C. Oehlschlager, and E. Czyzewska Tetrahedron Lett. 24 1983 5587
15. C.R. Johnson, and D.S. Dhanoa J. Org. Chem. 52 1987 1885
16. J.A. Marshall, and K.G. Pinney J. Org. Chem. 58 1993 1885
17. F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, and B.L. Feringa Tetrahedron Lett. 40 1999 4893
18. A. Fürstner, and M. Méndez Angew. Chem., Int. Ed. 42 2003 5355
19. K. Mori Tetrahedron 30 1974 1065
20. M. Ito, Y. Hirata, K. Tsukida, N. Tanaka, K. Hamada, R. Hino, and T. Fujiwara Chem. Pharm. Bull. 36 1988 3328
21. A. Braumeler, W. Brade, A. Haag, and C.H. Eugster Helv. Chim. Acta 73 1990 700
22. H. Kleijn, J. Meijer, G.C. Overbeek, and P. Vermeer Rec. Trav. Chim. Pays-Bas 101 1982 97
23. J. Kjellgren, H. Sundén, and K.J. Szabó J. Am. Chem. Soc. 127 2005 1787
24. J.G. Knight, S.W. Ainge, C.A. Baxter, T.P. Eastman, and S.J. Harwood J. Chem. Soc., Perkin Trans. 1 2000 3788
25. Substrate 1 was easily prepared by the epoxidation of the corresponding known eneyne with m-CPBA in moderate to good yields.
26. +). Found: 290.1688.
27. Chiral substrate (1R,2R)-1a was prepared by the asymmetric epoxidation of the corresponding eneyne using Shi's fructose-derived chiral ketone with oxone; Z.-X. Wang, G.-A. Cao, and Y. Shi J. Org. Chem. 64 1999 7646
28. Enantiomeric excess of the obtained (1R,2R)-3aa was determined by HPLC analysis (DAICEL CHIRALCEL AD).
29. N2′ attack of palladium catalyst: C.J. Elsevier, P.M. Stehouwer, H. Westmijze, and P. Vermeer J. Org. Chem. 48 1983 1103
30. J.A. Marshall, and N.D. Adams J. Org. Chem. 62 1997 367
31. P. Dixneuf, T. Guyot, M.D. Ness, and S.M. Roberts Chem. Commun. 1997 2083
32. T. Konno, M. Tanikawa, T. Ishihara, and H. Yamanaka Chem. Lett. 2000 1360
33. From the results that the reaction smoothly proceeded in the absence of water (Table 1, entries 1-5), the direct transmetallation of cationic allenylpalladium 5 to intermediate 8 would also be possible.
34. S. Kotha, K. Lahri, and D.K. Kashinath Tetrahedron 58 2002 9633