Regioselective anti-addition of phenols to propargylic oxiranes by palladium(0) catalyst

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3669-3672

  Yoshida, Masahiro ^a   Morishita, Yukio ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Addition; Oxiranes; Palladium; Phenols; Propargylic compounds

Indexed keywords

ALKENE DERIVATIVE; ALKYNE; ETHYLENE OXIDE DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; PHENOL DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 17844381891     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.138     Document Type: Article

References (35)

1. J. Tsuji Palladium Reagents and Catalysts: Innovations in Organic Synthesis 1995 Wiley New York pp 453
2. J. Tsuji, and I. Minami Acc. Chem. Res. 20 1987 140
3. J. Tsuji, and T. Mandai Angew. Chem., Int. Ed. Engl. 34 1995 2589
4. For recent examples of palladium-catalyzed reactions of propargylic compounds with nucleophiles: C. Fournier-Nguefack, P. Lhoste, and D. Sinou Synlett 1996 553
5. J.-R. Labrosse, P. Lhoste, and D. Sinou Tetrahedron Lett. 40 1999 9025
6. J.-R. Labrosse, P. Lhoste, and D. Sinou Org. Lett. 2 2000 527
7. Y. Kozawa, and M. Mori Tetrahedron Lett. 42 2001 4869
8. Y. Kozawa, and M. Mori Tetrahedron Lett. 43 2002 1499
9. C. Damez, J.-R. Labrosse, P. Lhoste, and D. Sinou Tetrahedron Lett. 44 2003 557
10. Y. Kozawa, and M. Mori J. Org. Chem. 68 2003 8068
11. M. Tsubakiyama, Y. Sato, and M. Mori Heterocycles 64 2004 27 and see also Ref. 5
12. H. Kleijn, J. Meijer, G.C. Overbeek, and P.J. Vermeer R. Netherlands Chem. Soc. 101 1982 97
13. I. Minami, M. Yuhara, H. Watanabe, and J. Tsuji J. Organomet. Chem. 334 1987 225
14. M.E. Piotti, and H. Alper J. Org. Chem. 62 1997 8484
15. J.G. Knight, S.W. Ainge, C.A. Baxter, T.P. Eastman, and S.J. Harwood J. Chem. Soc., Perkin Trans. 1 2000 3188
16. J. Kjellgren, H. Sundén, and K.J. Szabó J. Am. Chem. Soc. 127 2005 1787
17. M. Yoshida, H. Nemoto, and M. Ihara Tetrahedron Lett. 40 1999 8583
18. M. Yoshida, and M. Ihara Angew. Chem., Int. Ed. 40 2001 616
19. M. Yoshida, M. Fujita, T. Ishii, and M. Ihara J. Am. Chem. Soc. 125 2003 4874
20. M. Yoshida, M. Fujita, and M. Ihara Org. Lett. 5 2003 3325
21. M. Yoshida, Y. Komatsuzaki, H. Nemoto, and M. Ihara Org. Biomol. Chem. 2004 3099
22. M. Yoshida, and M. Ihara Chem. Eur. J. 2004 2886
23. 3: C, 78.23; H, 6.88. Found: C, 78.23; H, 6.90
24. 3 as a base
25. N2′ attack of palladium catalyst: C.J. Elsevier, P.M. Stehouwer, H. Westmijze, and P. Vermeer J. Org. Chem. 48 1983 1103
26. J.A. Marshall, and N.D. Adams J. Org. Chem. 62 1997 367
27. P. Dixneuf, T. Guyot, M.D. Ness, and S.M. Roberts Chem. Commun. 1997 2083
28. T. Konno, M. Tanikawa, T. Ishihara, and H. Yamanaka Chem. Lett. 2000 1360
29. K. Tsutsumi, T. Kawase, K. Kakiuchi, S. Ogoshi, Y. Okada, and H. Kurosawa Bull. Chem. Soc. Jpn. 72 1999 2687
30. S. Ogoshi, and H. Kurosawa J. Synth. Org. Chem. Jpn. 61 2003 14
31. B. Rickborn B.M. Trost Comprehensive Organic Synthesis Vol. 3 1991 Pergamon Oxford 733 Chapter 3.3 [N# 238]
32. Chiral substrate (1R,2R)-1a was prepared by the asymmetric epoxidation of 5 using Shi's fructose-derived chiral ketone with Oxone: Z.-X. Wang, G.-A. Cao, and Y. Shi J. Org Chem. 64 1999 7646
33. Enantiomeric excess of the obtained (1R,2R)-3aa was determined by HPLC analysis (DAICEL CHIRALCEL OF)
34. Similar type of the reaction about anti-addition of oxygen nucleophile to alkynes by palladium(0) catalysts has been previously reported. D.H. Camacho, S. Saito, and Y. Yamamoto Tetrahedron Lett. 43 2002 1085
35. For example: H. Zhang, and K.S. Gates Biochemistry 39 2000 14968