Intramolecular Baylis-Hillman and Morita reactions using unsaturated thiol ester substrates containing enolizable aldehydes

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3687-3690

  Keck, Gary E ^a   Welch, Dennie S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY;

ALDEHYDES; ESTERS; SULFHYDRYL COMPOUNDS;

EID: 0037126262     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026638s     Document Type: Article

References (18)

1. For reviews, see: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
2. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
3. Roth, F.; Gygax, P.; Frater, G. Tetrahedron Lett. 1992, 33, 1045.
4. Drewes, S. E.; Njamela, O. L.; Emslie, N. D.; Ramesar, N.; Field, J. S. Synth. Commun. 1993, 23, 2807.
5. Black, G. P.; Dinon, F.; Fratucello, S.; Murphy, P. J.; Nielsen, M.; Williams, H. L.; Walshe, N. D. A. Tetrahedron Lett. 1997, 38, 8561.
6. Dinon, F.; Richards, E.; Murphy, P. J.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A. Tetrahedron Lett. 1999, 40, 3279.
7. Richards, E. L.; Murphy, P. J.; Dinon, F.; Fratucello, S.; Brown, P. M.; Gelbrich, T.; Hursthouse, M. B. Tetrahedron 2001, 57, 7771.
8. Kataoka, T.; Iwama, T.; Kinoshita, H.; Tsujiyama, S.; Tsurukami, Y.; Iwamura, T.; Watanabe, S. Synlett 1999, 197.
9. Keck, G. E.; Boden, E. P.; Mabury, S. A. J. Org. Chem. 1985, 50, 709.
10. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
11. Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1983, 105, 1598.
12. For rate accelerations of bimolecular Baylis-Hillman reactions in protic media, see: (a) Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510.
13. (b) Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413.
14. DMAP has been used in the Baylis-Hillman reaction of cyclohexenone with aqueous formaldehyde: Rezgui, F.; El Gaied, M. M. Tetrahedron Lett. 1998, 39, 5965.
15. It has been suggested that DBU is the best amine promoter for the Baylis-Hillman reaction: Aggarwal, V. K.; Mereu, A. Chem. Commun. 1999, 2311.
16. Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
17. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
18. Neither author reported cyclizations in which the initial nucleophilic addition occurred to an enoate or thioenoate.