Selective remote functionalization of alkyl side chains in the coupling of Fischer carbene complexes with conjugated enediynes

Tetrahedron

Volumn 56, Issue 15, 2000, Pages 2175-2182

  Zhang, Yi ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

Coupling reaction; Derivatives; Fischer carbene complexes

Indexed keywords

ALKYL GROUP; CARBENE;

ALKYLATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFERENCE PAPER; PRIORITY JOURNAL;

EID: 0034616205     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01100-X     Document Type: Conference Paper

References (23)

1. For a recent review, see: Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198.
2. For the latest example, see Yan, J.; Matasi, J. J.; Zhu, J.; Herndon, J. W. J. Org. Chem. 1999, 64, 1291-1301.
3. Harvey D.F., Sigano D.M. Chem. Rev. 96:1996;271-288.
4. For a recent example, see: Ishibashi, T.; Mori, M. J. Org. Chem. 1997, 62, 7058-7060.
5. Herndon J.W., Hayford A. Organometallics. 14:1995;1556-1558.
6. For other mechanism based alternatives, see: (a) Wulff, W. D.; Kaesler, R. W.; Peterson, G. A.; Tang, P.-C. J. Am. Chem. Soc. 1985, 107, 1060-1062.
7. (b) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 7418-7420.
8. (c) Herndon, J. W.; Hayford, A. Organometallics 1995, 14, 1556-1558.
9. (d) Wulff, W. D. Adv. Met.-Org. Chem. 1989, 1, 209-393.
10. The only examples of this type of chromium carbene complex are aminocarbene complexes. (a) Aumann, R.; Heinen, H. Chem. Ber. 1986, 117, 3801-3811.
11. (b) Aumann, R.; Fischer, E. O. Chem. Ber. 1968, 101, 954-962.
12. Herndon J.W., Wang H. J. Org. Chem. 63:1998;4564-4565.
13. Herndon J.W., Wang H. J. Org. Chem. 63:1998;4562-4563.
14. Formation of β,γ-unsaturated benzene derivatives was a minor but significant reaction pathway in thermolyses of 4-(1-butynyl)-2-cyclobuten-one derivatives, which also involves enyne-ketene and diradical intermediates; formation of cyclic ethers analogous to 24 was generally the major reaction pathway. Xu, S. L.; Moore, H. W. J. Org. Chem. 1992, 57, 326-338.
15. Rahm A., Wulff W.D. J. Am. Chem. Soc. 118:1996;1807-1808.
16. Grissom J.W., Gunawardena G.U., Huang D. Tetrahedron. 52:1996;6453-6518.
17. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
18. (b) For a review see Curran, D. P. Synthesis 1988, 417-439.
19. Giese B., Hartung J. Chem. Ber. 125:1992;1777-1779.
20. For a discussion of similar resonance in the phenoxide-chromium complex, see: Heppert, J. A.; Boyle, T. J.; Takusagawa, F. Organometallics 1989, 8, 461-467.
21. Wang K.K., Liu B., Peterson J.L. J. Am. Chem. Soc. 118:1996;6860-6867.
22. Prepared from commercially-available (Lancaster) 3-nonyn-1-ol according to the procedure of Wulff. Wang, H.; Wulff, W. D. J. Am. Chem. Soc. 1998, 120, 10573-10574.
23. Chemin D., Linstrumelle G. Tetrahedron. 50:1994;5335-5344.