A novel route to fully substituted cyanoallenes from three components, ketones, chloromethyl p-tolyl sulfoxide, and nitriles, via α- bromocyclopropyl p-tolyl sulfoxides

Tetrahedron Letters

Volumn 47, Issue 16, 2006, Pages 2835-2838

  Satoh, Tsuyoshi ^a   Gouda, Youhei ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Allene; Cyanoallene; Lithium cyclopropylidene; Sulfoxide; Sulfoxide lithium exchange

Indexed keywords

1 CHLOROVINYL 4 TOLYLSULFOXIDE DERIVATIVE; ALLENE DERIVATIVE; ALPHA BROMOCYCLOPROPYL 4 TOLYLSULFOXIDE; ALPHA BROMOCYCLOPROPYL 4 TOLYLSULFOXIDE DERIVATIVE; ALPHA CHLOROCYCLOPROPYL 4 TOLYLSULFOXIDE; CHLOROMETHYL 4 TOLYLSULFOXIDE; ISOBUTYRONITRILE; KETONE DERIVATIVE; LITHIUM; NITRILE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 33644970625     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.161     Document Type: Article

References (38)

1. Some monographs and reviews concerning chemistries and synthesis of allenes: S. Patai The Chemistry of Ketenes, Allenes, and Related Compounds 1980 John Wiley and Sons Chichester Part 1 and 2
2. L. Brandsma, and H.D. Verkruijsse Synthesis of Acetylenes, Allenes, and Cumulenes 1981 Elsevier Amsterdam
3. H.F. Schuster, and G.M. Coppola Allenes in Organic Synthesis 1984 John Wiley and Sons New York
4. M.A. Point Tetrahedron 36 1980 331
5. D.J. Pasto Tetrahedron 40 1984 2805
6. R. Zimmer Synthesis 1993 165
7. M. Miesch Synthesis 2004 746
8. Allenes: application in synthesis (special topic); Synthesis 2004, pp 735-795.
9. Synthesis and properties of allenic natural products and pharmaceuticals: A. Hoffmann-Roder, and N. Krause Angew. Chem., Int. Ed. 43 2004 1196 and the references cited therein
10. M. Franck-Neumann, D. Martina, and D. Neff Tetrahedron: Asymmetry 9 1998 697
11. M. Oku, S. Arai, K. Katayama, and T. Shioiri Synlett 2000 493
12. W. von E. Doering, and P.M. LaFamme Tetrahedron 2 1958 75
13. W.R. Moore, and H.R. Ward J. Org. Chem. 25 1960 2073
14. L. Skattebol Tetrahedron Lett. 1961 167
15. W.R. Moore, and H.R. Ward J. Org. Chem. 27 1962 4179
16. For example: G.H. Posner Org. React. 22 1975 287
17. I. Marek, P. Mangeney, A. Alexakis, and J.F. Normant Tetrahedron Lett. 27 1986 5499
18. A. Alexakis, I. Marek, P. Mangeney, and J.F. Normant J. Am. Chem. Soc. 112 1990 8042
19. O.W. Gooding, C.C. Beard, D.Y. Jackson, D.L. Wren, and G.F. Cooper J. Org. Chem. 56 1991 1083
20. N. Krause, and A. Hoffmann-Roder Tetrahedron 60 2004 11671
21. C. Nativi, A. Ricci, and M. Taddei Tetrahedron Lett. 28 1987 2751
22. T. Konoike, and Y. Araki Tetrahedron Lett. 33 1992 5093
23. Y. Zhao, P. Quayle, and E.A. Kuo Tetrahedron Lett. 35 1994 3797
24. Y. Araki, and T. Konoike J. Synth. Org. Chem. Jpn. 58 2000 956
25. M.A. Tius, and S.K. Pal Tetrahedron Lett. 42 2001 2605
26. T. Satoh, N. Hanaki, Y. Kuramochi, Y. Inoue, K. Hosoya, and K. Sakai Tetrahedron 58 2002 2533
27. T. Satoh, T. Sakamoto, and M. Watanabe Tetrahedron Lett. 43 2002 2043
28. T. Satoh, T. Sakamoto, M. Watanabe, and K. Takano Chem. Pharm. Bull. 51 2003 960
29. T. Satoh, T. Kurihara, and K. Fujita Tetrahedron 57 2001 5369
30. T. Satoh, and H. Ota Tetrahedron 56 2000 5113
31. T. Satoh, M. Yoshida, Y. Takahashi, and H. Ota Tetrahedron: Asymmetry 14 2003 281
32. D. Wakasugi, and T. Satoh Tetrahedron 66 2005 1245
33. T. Kawashima, H. Kashima, D. Wakasugi, and T. Satoh Tetrahedron Lett. 46 2005 3767
34. T. Satoh, T. Kawashima, S. Takahashi, and K. Sakai Tetrahedron 59 2003 9599
35. T. Satoh, K. Takano, H. Ota, H. Someya, K. Matsuda, and M. Koyama Tetrahedron 54 1998 5557
36. G. Tsuchihashi, and K. Ogura Bull. Chem. Soc. Jpn. 44 1971 1726
37. T. Satoh, A. Kondo, and J. Musashi Tetrahedron 60 2004 5453
38. 31N: M, 273.2457. Found: m/z 273.2456.