Sequential 1,4-Addition and Ireland-Claisen Rearrangement Promoted by a Manganese-PbCl2-Me3SiCl System

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8728-8729

  Takai, Kazuhiko ^a   Ueda, Takashi ^a   Kaihara, Hiroya ^a   Sunami, Yoichi ^a   Moriwake, Toshio ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001286179     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9618482     Document Type: Article

References (33)

1. (a) Beckwith, A. L. J. Tetrahedron 1981,37, 3073.
2. (b) Stork, G. Current Trends in Organic Synthesis; Nozaki, H., Ed.; Pcrgamon Press: Oxford, 1983; p 359.
3. Ueno, Y. Synth. Org. Chem. Jpn. 1984, 42,1121.
4. Giese, B. Angew. Chem., Int. Ed. Engl. 1985,24, 553.
5. (e) Curran, D. P. Synthesis 1988,417, 489. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming,-I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 715.
6. (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897.
7. (b) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976,98, 2868.
8. Gajewski, J. J.; Erarani, J. J. Am. Chem. Soc. 1984, 706, 5733.
9. Ireland, R. E.; Wipf, P.; Armstrong, J. D., III. J. Org. Chem. 1991,56, 650.
10. (e) Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572. For reviews, see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Pereira, S.; Srebnik, M. Aldrichim. Acta 1993, 26, 17.
11. Sequential 1,4-addition and Ireland-Claisen rearrangement was accomplished with Grignard reagents under copper catalysis. Aoki, Y.; Kuwajima, I. Tetrahedron Lett. 1990, 31, 7457.
12. Hanamoto, T.; Baba, Y.; Inanaga, J. J. Org. Chem. 1993,58,299.
13. Takai, K.; Ueda, T.; Ikeda, N.; Moriwake, T. J. Org. Chem. 1996, 61, 7990.
14. Manganese powder was purchased from two sources: Rare Metallic Co. (99% purity, -80 mesh) and Kojundo Chemical Laboratory (99.9% purity, -50 mesh).
15. PbCl2 (99.99% purity) was purchased from Rare Metallic Co., Japan.
16. For activation of metals with MeaSiCI, see: Jhingan, A. K.; Maier, W. F. J. Org. Chem. 1987, 52, 1161.
17. Knöchel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
18. Takai, K.; Kakiuchi, T.; Utimoto, K. J. Org. Chem. 1994,59, 2671.
19. Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
20. Lautens, M.; Ren, Y. J. Org. Chem. 1996, 61, 2210.
21. Alkylmanganese compounds add to a,/î-unsaturated carbonyl compounds in a 1,4-fashion with the assistance of a catalytic amount of CuCl. Cahiez, G.; Alami, M. Tetrahedron Lett. 1989,30,3541, 7365.
22. For reactions of alkylmanganese compounds, see: Cahiez, G.; Figadere, B. Tetrahedron Lett. 1986,27, 4445.
23. Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989,30, 7369.
24. Kirn, S.-H. K.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197.
25. For Ireland-Claisen rearrangement via metal enolate of allylic esters, see: (a) Zn: Baldwin, J. E.; Walker, J. A. J. Chem. Soc., Chem. Commun. 1973, 117.
26. (b) B: Corey, E. J.; Lee, D.-H. J. Am. Chem. Soc. 1991, 113, 4026.
27. Bassindale, A. R.; Stout, T. Tetrahedron Lett. 1985, 26, 3403.
28. 2, -78 to +25°C, 70-35%.16 In the case of the Wittig olefination with benzylidenetripenylphosphorane (for Table 2, run 3), a mixture of olefins (ZIE = 26/74) was obtained.
29. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
30. Daumas, M.; Vo-Quang, Y.; Vo-Quang, L.; Le Goffic, F. Synthesis 1989, 64.
31. Bestmann, H. J.; Stransky, W.; Vostrowsky, O. Chem. Ber. 1976, 709, 1694.
32. 4, and concentrated in vacuo. Purification of the crude product by column chromatography on silica gel (hexane-ethyl acetate, 30:1) gave the ×, δ-unsaturated acid 3 (0.21 g, 0.92 mmol) in 92% yield.
33. 3SiCl produced E and Z ketene silyl acetals in a 44/56 ratio.