Cyclization of nonterminal alkynic β-Keto esters catalyzed by gold(I) complex with a semihollow, end-capped triethynylphosphine ligand

Organic Letters

Volumn 10, Issue 21, 2008, Pages 5051-5054

  Ito, Hideto ^a   Makida, Yusuke ^a   Ochida, Atsuko ^a   Ohmiya, Hirohisa ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 60949085568     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802079r     Document Type: Article

References (14)

1. For reviews on gold catalysis, see: (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
2. (b) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265.
3. (c) Arcadi, A. Chem. Rev. 2008, 108, 3266-3325.
4. (d) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350.
5. (e) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378.
6. For gold(I)-catalyzed cyclizations of acetylenic keto esters, see: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
7. (b) Staben, S. T.; Kennedy-Smith. J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350-5352.
8. (c) Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133-4136.
9. Ochida, A.; Sawamura, M. Chem.-Asian J. 2007, 2, 609-618.
10. For a review concerning the synthesis and applications of bowl-shaped phosphine ligands, whose steric feature is related to our triethynylphosphine ligands, see: Tsuji, Y.; Fujiwara, T. Chem. Lett. 2007, 36, 1296-1301.
11. Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486-16487.
12. 2.
13. 3 catalyst: 24 h; 41% conversion; 35% yield; 3e/4e, 12:88. 48 h; 44% conversion; 44% yield; 3e/4e, 12:88.
14. For the structure of an isolated gold(I)-alkyne complex, see: Shapiro, N. D.; Toste, F. D. Proc. Nat. Acad. Sci. U.S.A. 2008, 105, 2779-2782.