An alkoxide-directed carbometalation of internal alkynes

Journal of the American Chemical Society

Volumn 128, Issue 9, 2006, Pages 2764-2765

  Ryan, Jamie ^a   Micalizio, Glenn C ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; OXIDE;

ARTICLE; GRIGNARD REACTION; METALLATION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; PHASE TRANSITION; REACTION ANALYSIS; STEREOCHEMISTRY; TRANSESTERIFICATION;

EID: 33644962709     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057352w     Document Type: Article

References (26)

1. For a general review on substrate-directable reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
2. Some recent examples of heteroatom-directed C-C bond formation include: Directed allylic substitution reactions: (a) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. Tetrahedron 1998, 54, 1117-1130 and references therein,
3. (b) Itami, K.; Koike, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 6957-6958.
4. Phosphine-directed hydroformylation: (c) Krauss, I. J.; Wang, C. C.-Y.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 11514-11515.
5. N2′additionreactions: (d) Xie, C.; Nowak, P.; Kishi, Y. Org. Lett. 2002, 4, 4427-4429.
6. (e) Fürstner, A.; Méndez, M. Angew. Chem., Int. Ed. 2003, 42, 5355-5357.
7. Directed C-H activation/C-C bond formation: (f) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531.
8. (g) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692-9693.
9. For olefin-directed regioselective nickel-calalyzed reductive coupling reactions, see: (a) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698-3699.
10. (b) Miller, K. M.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 15342-15343.
11. For hydroxyl-directed carbometalation reactions based on titanium, see: (a) Coleman, R. A.; O'Doherty, C. M.; Tweedy, H. E.; Harris, T. V.; Thompson, D. W. J. Organomet. Chem. 1976, 107, C15-C17.
12. For hydroxyl-directed carbometalation based on magnesium, see: (b) Eisch, J. J.; Merkley, J. H. J. Organomet. Chem. 1969, 20, P27-P31.
13. (c) Richey, H. G.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-P35.
14. (d) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080.
15. (e) Itami, K.; Mitsudo, K.; Yoshida, J. Angew. Chem., Int. Ed. 2001, 40, 2337-2339.
16. For directed carbometalation based on tantalum, see: (f) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K. J. Org. Chem. 1994, 59, 5852-5853.
17. For directed carbometalation based on aluminum/zirconium, see: (g) Ma, S.; Negishi, E. J. Org. Chem. 1997, 62, 784-785.
18. For coupling of TMS-substituted alkynes and 2-alkynoates with terminal alkynes, see: (a) Hamada, T.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1999, 121, 7342-7344.
19. For regioselective coupling of internal alkynes bearing branched polyketide architecture with terminal alkynes, see: (b) Shimp, H. L.; Micalizio, G. C. Org. Lett. 2005, 7, 5111-5114.
20. For a report describing the effect of a tethered alkoxide in regioselective reductive coupling reactions of internal alkynes and aldehydes, see: (c) Bahadoor, A.; Micalizio, G. C. Org. Lett. 2006, 8, in press.
21. For examples of metallacyclopropanes bearing a tethered alkoxide (presumed formation of intermediate saturated oxabicyclo[3.1.0] titana-cyclopropanes), see: (a) Shevchuk, T. A.; Kulinkovich, O. G. Russ. J. Org. Chem. 2000, 36, 1124-1126.
22. (b) Quan, L. G.; Kim, S.; Lee, J. C.; Cha, J. K. Angew. Chem., Int. Ed. 2002, 41, 2160-2162.
23. (c) Masalov, N.; Cha, J. K. Org. Lett. 2004, 6, 2365-2368.
24. (d) Epstein, O. L.; Seo, J. M.; Masalov, N.; Cha, J. K. Org. Lett. 2005, 7, 2105-2108.
25. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206.
26. The other regioisomer possible was prepared independently and compared to the product mixture obtained from this reaction. The regioselectivity was then determined based on the signal-to-noise ratio of the spectrum. See Supporting Information for details.