A Facile One-Pot Synthesis of Homopropargylic Alcohols from Terminal Acetylenes

Journal of Organic Chemistry

Volumn 58, Issue 2, 1993, Pages 528-532

  Burns, Mark R ^a   Coward, James K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2242485132     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00054a047     Document Type: Note

References (24)

1. Broom, A. D. J. Med. Chem. 1989, 32, 2.
2. Yau, E. K.; Coward, J. K. J. Org. Chem. 1990, 55, 3147.
3. Gelin, R.; Gelin, S.; Albrand, M. Bull. Chem. Soc. Fr. 1971, 4546.
4. Epsztein, R. In Comprehensive Carbanion Chemistry; Buncel, F., Purst, T., Eds.; Elsevier: New York, 1984; part B, p 107.
5. Klein, J. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; part 1, p 343.
6. Zweifel, G.; Backlund, S. J.; Leung, T. J. Am. Chem. Soc. 1978, 100, 5561.
7. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579.
8. Furuta, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768.
9. Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870.
10. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198.
11. Yanagisama, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969.
12. Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441.
13. Rozema, M. J.; Knochel, P. Tetrahedron Lett. 1991, 32, 1855.
14. The alkynyl copper species was obtained by transmetalation of the corresponding lithium acetylide. House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 3893.
15. Corey, E. J.; Seebach, D.; Freedman, R. J. Am. Chem. Soc. 1967, 89, 434.
16. Rozema, M. Ph.D. Thesis, The University of Michigan, Ann Arbor, MI, May, 1992.
17. Wittig, G.; Wingler, F. Chem. Ber. 1964, 97, 2139;
18. Chem. Ber. 2146.
19. The formation of 7c and 11c from the reaction of ethoxyacetylene (4f) and n-BuLi under the conditions described is assumed to occur via n-BuLi attack at the electrophilic α-carbon atom followed by elimination of ethanol. The resulting 1-copper hexynyl species can then proceed to give the observed products as before. For a review of chemistry of ethynyl ethers and thioethers, see: Arens, J. F. Adv. Org. Chem. 1960, 2, 117.
20. Yamamoto, K.; Hayashi, A.; Suzuki, S.; Tsuji, J. Organometallics 1987, 6, 974.
21. Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 431.
22. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
23. Padwa, A.; Rodriquez, A.; Tohidi, M.; Kukunaga, T. J. Am. Chem. Soc. 1983, 105, 933.
24. Yau, E. K.; Coward, J. K. Aldrichim. Acta 1988, 21, 106.