LDA-catalyzed cycloisomerization of 2-(2-propynyloxy)ethyl iodides leading to 3-(iodomethylene)tetrahydrofurans

Organic Letters

Volumn 7, Issue 5, 2005, Pages 779-781

  Harada, Toshiro ^a   Muramatsu, Keiko ^a   Fujiwara, Takayuki ^a   Kataoka, Hiroshi ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; CARBENOID; IODINE DERIVATIVE; LITHIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; ISOMERIZATION; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 15044361356     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047570e     Document Type: Article

References (19)

1. (a) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489.
2. (b) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chcm. Soc. 1989, 111, 6265.
3. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140-3157.
4. (a) Ichinose, Y.; Matsunaga, S.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155.
5. (b) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604.
6. (c) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041.
7. (a) Chakraborty, A.; Marek, I. Chem. Commun. 1999, 2375-2376.
8. (b) Yanada, R.; Koh, Y.; Nishimori, N.; Matsumura, A.; Obika, S.; Mitsuya, H.; Fujii, N.; Takemoto, Y. J. Org. Chem. 2004, 69, 2417.
9. Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents: Academic Press: London: 1988; 283.
10. (a) Merril, R. E.; Allen, J. L.; Abramovitch, A.; Negishi, E. Tetrahedron Lett. 1977, 1019.
11. (b) Corey, E. J.; Seibel, W. L. Tetrahedron Lett. 1986, 27, 909.
12. (c) Negishi, E.; Nguyen, T.; Boardman, L. D.; Sawada, H.; Morrison, J. A. Heteroatom Chem. 1992, 3, 293.
13. (a) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1995, 60, 5370.
14. (b) Harada, T.; Otani, T.; Oku, A. Tetrahedron Lett. 1997, 38, 2855.
15. Harada, T.; Iwazaki, K.; Otani, T.; Oku, A. J. Org. Chem. 1998, 63, 9007.
16. Some transition metal acetylides are known to react with electrophiles at the β position to form vinylidene complexes: Bruce. M. I. Chem. Rev. 1991, 91, 197.
17. Harada, T.; Fujiwara, T.; Iwazaki, K.; Oku, A. Org. Lett. 2000, 2, 1855.
18. Knorr, R. Chem. Rev. 2004, 104, 3795.
19. The corresponding tandem cyclization product 2 (R = Ph, X = O, n = 1) was obtained in 10% yield.