Synthetic Routes to Allenic Acids and Esters and Their Stereospecific Conversion to Butenolides

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 367-371

  Marshall, James A ^a   Wolf, Mark A ^a   Wallace, Eli M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000725878     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9618740     Document Type: Article

References (20)

1. Cf. (a) Marshall, J. A.; Bartley, G. S.; Wallace, E. M. J. Org. Chem. 1996, 61, 5729. (b) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 4247.
2. Cf. (a) Marshall, J. A.; Bartley, G. S.; Wallace, E. M. J. Org. Chem. 1996, 61, 5729. (b) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 4247.
3. For a recent review, see: Knight, D. W. Contemp. Org. Synth. 1994, 1, 287.
4. (a) Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
5. (b) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550.
6. Lang, R. W.; Hansen, H. J. Helv. Chim. Acta 1980, 63, 438.
7. Manchand, P. S. J. Chem. Soc., Chem. Commun. 1971, 667.
8. For other Ag(I)-catalyzed cyclizations leading to exocyclic enol lactones, see: Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 28, 6447. Dalla, V.; Pale, P. Tetrahedron Lett. 1994, 35, 3525.
9. For other Ag(I)-catalyzed cyclizations leading to exocyclic enol lactones, see: Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 28, 6447. Dalla, V.; Pale, P. Tetrahedron Lett. 1994, 35, 3525.
10. Tsuji, J. Sugiura, T.; Minami, I. Tetrahedron Lett. 1986, 27, 731.
11. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
12. 3 signals. Subsequent analysis by HPLC was in close agreement.
13. Cf. Smith, A. B., III; Duan, J. J.-W.; Hull, K. G.; Salvatore, B. A. Tetrahedron Lett. 1991, 32, 4855.
14. Racemization of allenyl/propargyl Pd intermediates has previously been studied. Granberg, K. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 6858.
15. Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 452.
16. 8
17. Marshall, J. A.; Wolf, M. A. J. Org. Chem. 1996, 61, 3238.
18. Yadav, J. S.; Chandler, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455. Takano, S.; Yoshimitsu, T.; Ogasawara, K. Synlett 1994, 119.
19. Yadav, J. S.; Chandler, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455. Takano, S.; Yoshimitsu, T.; Ogasawara, K. Synlett 1994, 119.
20. 3 at 300 and 75 MHz, respectively.