Alkenylation of thiophenes and furans at the 2-position and a synthesis of allenes conjugated with α,β-unsaturated ester with magnesium alkylidene carbenoids

Tetrahedron

Volumn 65, Issue 17, 2009, Pages 3509-3517

  Mori, Natsuki ^a   Obuchi, Kazumi ^a   Katae, Takashi ^a   Sakurada, Jo ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alkenylation; Furan; Magnesium alkylidene carbenoid; Magnesium carbenoid; Thiophene

Indexed keywords

1 CHLOROVINYL 4 TOLYLSULFOXIDE DERIVATIVE; ALKENYL GROUP; ALKYL GROUP; ALLENE DERIVATIVE; CARBENOID; CHLOROMETHYL 4 TOLYLSULFOXIDE; ELECTROPHILE; ESTER DERIVATIVE; FURAN DERIVATIVE; KETONE DERIVATIVE; MAGNESIUM DERIVATIVE; SULFOXIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ALKENYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 62549089143     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.019     Document Type: Article

References (39)

1. Some monographs and reviews with regard to the chemistry of carbenes and carbenoids:
2. Kirmse W. Carbene Chemistry (1971), Academic, New York, NY
3. Dorwald F.Z. Metal Carbenes in Organic Synthesis (1999), Wiley-VCH, Weinheim
4. In: Bertrand G. (Ed). Carbene Chemistry (2002), Marcel Dekker, New York, NY
5. Kobrich G. Angew. Chem., Int. Ed. Engl. 11 (1972) 473
6. Stang P.J. Chem. Rev. 78 (1978) 383
7. Burke S.D., and Grieco P.A. Org. React. 26 (1979) 361
8. Schaefer III H.F. Acc. Chem. Res. 12 (1979) 288
9. Wynberg H., and Meijer E.W. Org. React. 29 (1982) 1
10. Taylor K.G. Tetrahedron 38 (1982) 2751
11. Oku A., and Harada T. J. Synth. Org. Chem. Jpn. 44 (1986) 736
12. Oku A. J. Synth. Org. Chem. Jpn. 48 (1990) 710
13. Adams J., and Spero D.M. Tetrahedron 47 (1991) 1765
14. Padwa A., and Weingarten M.D. Chem. Rev. 96 (1996) 223
15. Zaragoza F. Tetrahedron 53 (1997) 3425
16. Kirmse W. Angew. Chem., Int. Ed. 36 (1997) 1164
17. Braun M. Angew. Chem., Int. Ed. 37 (1998) 430
18. Mehta G., and Muthusamy S. Tetrahedron 58 (2002) 9477
19. Muller P. Acc. Chem. Res. 37 (2004) 243
20. Knorr R. Chem. Rev. 104 (2004) 3795
21. Doering W.v.E., Buttery R.G., Laughlin R.G., and Chaudhuri N. J. Am. Chem. Soc. 78 (1956) 3224
22. Satoh T. Chem. Soc. Rev. 36 (2007) 1561
23. Satoh T. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organomagnesium Compounds (2008), John Wiley and Sons, Chichester, UK 717-769
24. Satoh T., Sakamoto T., Watanabe M., and Takano K. Chem. Pharm. Bull. 51 (2003) 966
25. Satoh T., Takano K., Ota H., Someya H., Matsuda K., and Koyama M. Tetrahedron 54 (1998) 5557
26. Preliminary results of this study were reported as a letter:. Satoh T., Mori N., and Obuchi K. Tetrahedron Lett. 48 (2007) 6453
27. Satoh T., Kawashima T., Takahashi S., and Sakai K. Tetrahedron 59 (2003) 9599
28. Sugiyama S., and Satoh T. Tetrahedron: Asymmetry 16 (2005) 665
29. Some papers for the alkenylation of thiophenes:
30. Li Y., Li Z., Li F., Wang Q., and Tao F. Tetrahedron Lett. 46 (2005) 6159
31. Wu M.-Y., Yang F.-Y., and Cheng C.-H. J. Org. Chem. 64 (1999) 2471
32. Zeni G., Alves D., Braga A.L., Stefani H.A., and Nogueira C.W. Tetrahedron Lett. 45 (2004) 4823
33. Tsukada N., Murata K., and Inoue Y. Tetrahedron Lett. 46 (2005) 7515
34. Hong P., Cho B.-Re., and Yamazaki H. Chem. Lett. (1980) 507
35. Maruyama O., Yoshidomi M., Fujiwara Y., and Taniguchi H. Chem. Lett. (1979) 1229
36. Watanabe M., Nakamura M., and Satoh T. Tetrahedron 61 (2005) 4409
37. Taschner M.J., and Kraus G.A. J. Org. Chem. 43 (1978) 4235
38. Atsumi K., and Kuwajima I. J. Am. Chem. Soc. 101 (1979) 2208
39. Takanishi K., Urabe H., and Kuwajima I. Tetrahedron Lett. 28 (1987) 2281