An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels-Alder reactions

Canadian Journal of Chemistry

Volumn 84, Issue 10, 2006, Pages 1487-1503

  Heller, Douglas P ^a   Goldberg, Daniel R ^a   Wu, Hongqiao ^a   Wulff, William D ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Diels Alder; VANOL; VAPOL; Vaulted biaryl ligands

Indexed keywords

ASYMMETRIC CATALYSIS; DIELS ALDER REACTION; DIELS ALDER REACTIONS; VANOL; VAPOL; VAULTED BIARYL LIGANDS;

ALUMINUM; CATALYSIS; LIGANDS; PHENOLS; REACTION KINETICS;

DERIVATIVES;

3,5 DI TERT BUTYLBROMOBENZENE; 3,5 DI TERT BUTYLPHENYL; 6,6' DIBROMO 2,2' DIPHENYL 3,3' BIS(PHENANTHREN 4 OL); ACRYLIC ACID METHYL ESTER; AMIDE; BENZENE DERIVATIVE; BORONIC ACID DERIVATIVE; CATECHOL KETAL; CHROMIUM CARBENE; CYCLOPENTADIENE DERIVATIVE; LEWIS ACID; LIGAND; METHACROLEIN; PHENANTHRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIELS ALDER REACTION; GRIGNARD REACTION; STRUCTURE ANALYSIS;

EID: 33847688903     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-124     Document Type: Article

References (29)

1. J.M. Brunel. Chem. Rev. 105, 857 (2005)
2. (a) L. Pu. Chem. Rev. 98, 2405 (1998);
3. (b) P. Kocovsky, S. Vyskocil, and M. Smrcina. Chem. Rev. 103, 3213 (2003);
4. (c) Y. Chen, S. Yekta, and A.K. Yudin. Chem. Rev. 103, 3155 (2003).
5. J. Bao, W.D. Wulff, J.D. Dominy, M.J. Fumo, E.B. Grant, A.C. Rob, M.C. Whitcomb, S. Yeung, R.L. Ostrander, and A. Rheingold. J. Am. Chem. Soc. 118, 3392 (1996).
6. (a) J. Bao, W.D. Wulff, and A.L. Rheingold. J. Am. Chem. Soc. 115, 3814 (1993);
7. (b) J. Bao and W.D. Wulff. Tetrahedron Lett. 36, 3321 (1995);
8. (c) D.P. Heller, D.R. Goldberg, and W.D. Wulff. J. Am. Chem. Soc. 119, 10551 (1997).
9. (a) J.C. Antilla and W.D. Wulff. J. Am. Chem. Soc. 121, 5099 (1999);
10. (b) J. Antilla and W.D. Wulff. Angew. Chem. Int. Ed. 39, 4518 (2000);
11. (c) C. Loncaric and W.D. Wulff. Org. Lett. 3, 3675 (2001);
12. (d) A.P. Patwardhan, V.R. Pulgam, Y. Zhang, and W.D. Wulff. Angew. Chem. Int. Ed. 44, 6169 (2005).
13. S. Xue, S. Yu, Y.-H. Deng, and W.D Wulff. Angew. Chem. Int. Ed. 40, 2271 (2001).
14. C. Bolm, J. Frison, Y. Zhang, and W.D. Wulff. Synlett, 1619 (2004).
15. G.B. Rowland, H. Zhang, E.B. Rowland, S. Chennamadhavuni, Y. Wang, and J.C. Antilla. J. Am. Chem. Soc. 127, 15696 (2005).
16. E. Napolitano, R. Fiaschi, and E. Mastrorilli. Synthesis, 122 (1986).
17. W.D. Wulff, B.M. Bax, T.A. Brandvold, K.S. Chan, A.M. Gilbert, R.P. Hsung, J. Mitchell, and J. Clardy. Organometallics, 13, 102 (1994).
18. M. Smrcina, M. Lorenc, V. Hanus, P. Sedmera, and P. Kocovsky. J. Org. Chem. 57, 1917 (1992).
19. Y. Zhang, S.-M. Yeung, H. Wu, D.P. Heller, C. Wu, and W.D. Wulff. Org. Lett. 5, 1813 (2003).
20. M. Kumada, K. Tamao, and K. Sumitani. Org. Syn. Coll. Vol. VI. 409 (1988).
21. N. Miyaura, T. Yanagi, and A. Suzuki. Synth. Commun. 11, 513 (1981).
22. For recent examples and reviews, see: (a) A.M. Costa, C. Garcia, P.J. Carroll, and P.J. Walsh. Tetrahedron, 61, 6442 (2005);
23. (b) B.M. Trost, A. Fettes, and B.T. Shireman. J. Am. Chem. Soc. 126, 2660 (2004);
24. (c) M.H. Todd. Chem. Soc. Rev. 31, 211 (2002).
25. M.S. Newman and S. Seshadri. J. Org. Chem. 27, 76 (1962).
26. W. Brackman and P.J. Smit. Recl. Trav. Chim. Pays-Bas, 85, 857 (1966).
27. W.J. Thompson and J. Gaudino. Org. Chem. 49, 5237 (1984).
28. J.M. Mellor and C.F. Webb. J. Chem. Soc. Perkin Trans. 2, 17 (1974).
29. F. Furuta, S. Shimizu, Y. Miwa, and H. Yamamoto. J. Org. Chem. 54, 1483 (1989).