Synthesis of Morita-Baylis-Hillman-type adducts by unprecedented reaction of 1-phenyl-2-(trimethylsilyl)acetylene with aromatic aldehydes catalyzed by quaternary ammonium fluorides derived from cinchonine

Tetrahedron Letters

Volumn 46, Issue 41, 2005, Pages 7059-7063

  Yoshizawa, Kazuhiro ^a   Shioiri, Takayuki ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

Allenolate; Cinchonine; Morita Baylis Hillman adduct; Quaternary ammonium fluoride

Indexed keywords

1 PHENYL 2 (TRIMETHYLSILYL)ACETYLENE; ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; AMMONIUM FLUORIDE; CINCHONINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MORITA BAYLIS HILLMAN REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 24344500222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.057     Document Type: Article

References (31)

1. S. Colonna, H.H. Hiemstra, and H. Wynberg J. Chem. Soc., Chem. Commun. 1978 238 239
2. A. Ando, T. Miura, T. Tatematsu, and T. Shioiri Tetrahedron Lett. 34 1993 1507 1510
3. K. Iseki, T. Nagai, and Y. Kobayashi Tetrahedron Lett. 35 1994 3137 3138
4. T. Shioiri, A. Bohsako, and A. Ando Heterocycles 42 1996 93 97
5. T. Shioiri, A. Ando, M. Masui, T. Miura, T. Tatematsu, A. Bohsako, M. Higashiyama, and C. Asakura M.E. Halpern Phase-Transfer Catalysis: Mechanism and Syntheses ACS Symposium Series 659 1997 American Chemical Society Washington, DC Chapter 11
6. M. Horikawa, J. Bush-Peterson, and E.J. Corey Tetrahedron Lett. 40 1999 3843 3846
7. E.J. Corey, and F.-Y. Zhang Angew. Chem., Int. Ed. 38 1999 1931 1934
8. E.J. Corey, and F.-Y. Zhang Org. Lett. 2 2000 4257 4259
9. G. Bluet, and J.-M. Campagne J. Org. Chem. 66 2001 4293 4298
10. S. Caron, N.M. Do, P. Arpin, and A. Larivee Synthesis 2003 1693 1698
11. For other chiral quaternally ammonium fluorides, see: T. Ooi, and K. Maruoka Acc. Chem. Res. 37 2004 526 533
12. H.-Y. Li L.A. Paquette Encyclopedia of Reagents for Organic Synthesis Vol. 7 1995 John Wiley & Sons New York 4728 4732
13. A. Bohsako, C. Asakura, and T. Shioiri Synlett 1995 1033 1034
14. E. Nakamura, and I. Kuwajima Angew. Chem., Int. Ed. Engl. 15 1976 498 499
15. A.B. Holmes, C.L.D. Jennings-White, and A.H. Schulthess J. Chem. Soc., Chem. Commun. 1979 840 842
16. E. Abele, K. Rubina, R. Abele, J. Popelis, I. Mazeika, and E. Lukevics J. Organomet. Chem. 586 1999 184 189
17. For recent reports about the Morita-Baylis-Hillman reactions and applications, see: D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
18. J.E. Yeo, X.L. Yang, H.J. Kim, and S. Koo Chem. Commun. 2004 236 237
19. S. Xue, L. He, K.-Z. Han, Y.-K. Liu, and Q.-X. Guo Synlett 2005 1247 1250 and references cited therein
20. The addition of α-silyl-α,β-unsaturated ketones to aldehydes catalyzed by TBAF affords the Morita-Baylis-Hillman-type adduct. See: K. Matsumoto, K. Oshima, and K. Utimoto Chem. Lett. 1994 1211 1214
21. The quaternary ammonium acetylide was considered to be generated in situ. Isolation or physical evidence of the quaternary ammonium acetylide has not been reported. See: T. Ishikawa, T. Mizuta, K. Hagiwara, T. Aikawa, T. Kudo, and S. Saito J. Org. Chem. 68 2003 3702 3705
22. The use of anhydrous TBAF also gave the addition product 4 as the major one. For the preparation of anhydrous TBAF, see: H. Sun, and S.G. DiMagno J. Am. Chem. Soc. 127 2005 2050 2051
23. B.M. Trost, and S. Oi J. Am. Chem. Soc. 123 2001 1230 1231
24. It was recognized that the silyl ether of the Z-isomer 9 isomerized to the E-isomer under basic conditions. For isomerization of the derivative of 2-benzylidene-1-indanone, see: B.D. Pearson, R.P. Ayer, and N.H. Cromwell J. Org. Chem. 27 1962 3038 3044
25. D.N. Kevill, E.D. Weiler, and N.H. Cromwell J. Org. Chem. 29 1964 1276 1278
26. Silyl allenolates afford Morita-Hillman-type adducts, see: M. Kato, and I. Kuwajima Bull. Chem. Soc. 57 1984 827 830
27. M.A. Tius, and H. Hu Tetrahedron Lett. 39 1998 5937 5940
28. A. Kaur, G. Kaur, and S. Trehan Indian J. Chem. 37B 1998 1048 1050
29. I.A. Stergiades, and M.A. Tius J. Org. Chem. 64 1999 7547 7551
30. G. Li, H.-X. Wei, B.S. Phelps, D.W. Purkiss, and S.H. Kim Org. Lett. 3 2001 823 826
31. For the synthesis of allenes by isomerization, see: N. Krause A.S.K. Hashmi Modern Allene Chemistry Vol. 1 2004 Wiley-VCH Weinheim