Bismuth-catalyzed intramolecular carbo-oxycarbonylation of 3-alkynyl esters

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5119-5122

  Komeyama, Kimihiro ^a   Takahashi, Keita ^a   Takaki, Ken ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; BISMUTH; ESTER; KETONE;

ARTICLE; CATALYSIS; CHEMISTRY;

ALDEHYDES; ALKYNES; BISMUTH; CATALYSIS; ESTERS; KETONES;

EID: 58149204346     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8019567     Document Type: Article

References (19)

1. (a) Fleming, I. Frontier Orbital and Organic Chemical Reactions; John Wiley & Sons, Ltd.: London, 1976.
2. (b) Ho, T.-L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic Press: New York, 1977.
3. (c) Woodward, S. Tetrahedron 2002, 58, 1017.
4. (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
5. (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
6. (a) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
7. (b) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
8. σ-π Chelation of typical metals was reported by Yamamoto et al.; see: Asao, N.; Asano, T.; Ohishi, T.; Yamamoto, Y, J. Am. Chem. Soc. 2000, 122, 4817.
9. (a) Komeyama, K.; Morimoto, T.; Takaki, K. Angew. Chem., Int. Ed. 2006, 45, 2938.
10. (b) Komeyama, K.; Morimoto, T.; Nakayama, Y.; Takaki, K. Tetrahedron Lett. 2007, 48, 3259.
11. (c) Komeyama, K.; Mieno, Y.; Yukawa, S.; Morimoto, T.; Takaki, K. Chem. Lett. 2007, 36, 752.
12. (d) Komeyama, K.; Takahashi, K.; Takaki, K. Chem. Lett. 2008, 37, 602.
13. (e) Komeyama, K.; Miyagi, M.; Takaki, K. Heteroatom Chem. 2008, 19, 644-648.
14. Fürstner has reported similar reactions using platinum and gold catalysts; see ref 3b and: Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024.
15. 6, (M = K or Cu) systems as σ- and π-acids was postulated by Shibasaki and Matsunaga et al.: Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 1611.
16. 5d we found that the iron- and the bismuth-catalyzed addition of heteroatom to alkynes seems to mainly proceed at the alkynyl carbon attached with aryl group. Furthermore, treatment of product 2r′ with NaOH (5 equiv) for 3 h in methanol provided 2-(2-benzhydrylhexanoyl-)benzoic acid in 47% yield.
17. (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
18. (b) Tayama, E.; Isaka, W. Org. Lett. 2006, 8, 5437.
19. Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W. Adv. Synth. Catal. 2006, 348, 1033.