Construction of chiral quaternary carbon centers via palladium-catalyzed asymmetric deconjugative allylation

Heterocycles

Volumn 76, Issue 2, 2008, Pages 1485-1495

  Yamamoto, Hiroki ^a   Oonishi, Yoshihiro ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Asymmetric Synthesis; Chiral Quaternary Carton Center; Deconjugative Alkylation; Knoevenagel Reaction; Palladium

Indexed keywords

EID: 61349145079     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)112     Document Type: Article

References (24)

1. Cope A.C., Holmes H.L., and House H.O. Org. React. 9 (1957) 107
2. Tsuboi S., Fujita H., Muranaka K., Seko K., and Takeda A. Chem. Lett. (1982) 1909
3. Tsuboi S., Muranaka K., Sakai T., and Takeda A. J. Org. Chem. 51 (1986) 4944
4. Kasatkin A.N., Biktimirov R.Kh., and Tolstikov G.A. Izv. Akad. Nauk. SSSR, Ser. Khim. 12 (1989) 2872
5. Sato Y., Oonishi Y., and Mori M. J. Org. Chem. 68 (2003) 9858
6. For reviews on asymmetric construction of quaternary carbon centers, see:. Fuji K. Chem. Rev. 93 (1993) 2037
7. Corey E.J., and Guzman-Perez A. Angew. Chem. Int. Ed. 37 (1998) 388
8. Christoffers J., and Mann A. Angew. Chem. Int. Ed. 40 (2001) 4591
9. Denissova I., and Barriault L. Tetrahedron 59 (2003) 10105
10. Douglas C.J., and Overman L.E. Proc. Nad. Acad. Sci. USA 101 (2004) 5363
11. Christoffers J., and Baro A. Adv. Synth. Catal. 347 (2005) 1473
12. Cozzi P.G., Hilgraf R., and Zimmermann N. Eur. J. Org. Chem. (2007) 5969
13. 2-carbon centers via a deconjugative Michael addition using a Cinchona alkaloid as an organic catalyst has been reported, see:. Bell M., Frisch K., and Jørgensen K.A. J. Org. Chem. 71 (2006) 5407
14. Kasatkin A.N., Biktimirov R.Kh., and Khailov L.M. Zh. Org. Khim. 26 (1990) 1191
15. Grubbs R.H., and DeVries R.A. Tetrahedron Lett. 26 (1977) 1879
16. Trost B.M., and Murphy D.J. Organometallics 4 (1984) 1143
17. Saito T., Yokozawa T., Ishizaki T., Moroi T., Sayo N., Miura T., and Kumobayashi H. Adv. Synth. Catal. 343 (2001) 264
18. von Matt P., and Pfaltz A. Angew. Chem., Int. Ed. Engl. 32 (1993) 566
19. Dawson G.J., Frost C.G., Williams J.M.J., and Coate S.W. Tetrahedron Lett. 34 (1993) 3149
20. Sprinz J., and Helmchen G. Tetrahedron Lett. 34 (1993) 1769
21. Hayashi T. Pure Appl. Chem. 60 (1988) 7
22. Trost B.M., and Van Vranken D.L. Angew. Chem., Int. Ed. Engl. 31 (1992) 228
23. Trost B.M., and Bunt R.C. Angew. Chem., Int. Ed. Engl. 35 (1996) 99
24. The substrate 4d was synthesized according to the literature, see:. Fleming F.F., Huang A., Sharief V.A., and Pu Y. J. Org. Chem. 64 (1999) 2830