A simple, reliable, catalytic asymmetric allylation of ketones

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3697-3699

  Waltz, Karen M ^a   Gavenonis, Jason ^a   Walsh, Patrick J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Alcohols; Allylation; Asymmetric catalysis; Titanium

Indexed keywords

ALCOHOLS; CATALYSIS;

ENANTIOSELECTIVITIES; QUARTERNARY STEREOGENIC CENTERS;

KETONES;

2 PROPANOL; ACETOPHENONE DERIVATIVE; ALDEHYDE; ALLYL ALCOHOL; ALLYL COMPOUND; KETONE; KETONE DERIVATIVE; LEWIS ACID; METHYL 2 NAPHTHYLKETONE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

ALLYL COMPOUNDS; CATALYSIS; KETONES; MOLECULAR STRUCTURE;

EID: 0037020373     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3697::AID-ANIE3697>3.0.CO;2-U     Document Type: Article

References (34)

1. Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
2. J. A. Marshall, Chem. Rev. 1996, 96, 31-48.
3. A. Yanagisawa in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin. 1999. p. 965-979.
4. A.L. Costa, M. G. Piazza, C. Tagliavini. A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001-7002.
5. G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544.
6. G. E. Keck, L. S. Geraci, Tetrahedron Lett. 1993, 34, 7827-7828.
7. G. E. Keck, K. Tarbet, L. S. Geraci, J. Am. Chem. Soc. 1993, 115, 8467-8468.
8. P. Bedeschi, S. Casolari, A. L. Costa, E. Tagliavini, A. Umani-Ronchi. Tetrahedron Lett. 1995, 36, 7897-7900.
9. S. Casolari, P. G. Cozzi, P. Orioli, E. Tagliavini, A. Umani-Ronchi, Chem. Commun. 1997, 2123-2124.
10. S, Weigand, R. Bürckner, Chem. Eur. J. 1996, 2, 1077-1084.
11. A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723-4724.
12. C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
13. H. Doucet, M. Santelli, Tetrahedron: Asymmetry 2000, 11, 4163-4169.
14. S. Kii, K. Maruoka, Tetrahedron Lett. 2001, 42, 1935-1939.
15. J. W. Faller, D. W. I. Sams, X. Lu, J. Am. Chem. Soc. 1996, 118, 1217-1218.
16. H. Hanawa, S. Kii, K. Maruoka, Adv. Synth. Catal. 2001, 1, 57-60.
17. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401.
18. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401.
19. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
20. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597.
21. M. Yasuda, N. Kitahara, T. Fujibayashi, A. Baba, Chem. Lett. 1998, 8, 743-744.
22. S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 1, 1061-1063.
23. A. Cunningham, S. Woodward, Synthesis 2002, 43-44.
24. J. Balsells, P. J. Walsh, J. Am. Chem. Soc. 2000, 122, 1802-1803.
25. J. Balsells, J. M. Betancort, P. J. Walsh, Angew. Chem. 2000, 112, 3570-3572; Angew. Chem. Int. Ed. 2000, 39, 3428-3430.
26. J. Balsells, J. M. Betancort, P. J. Walsh, Angew. Chem. 2000, 112, 3570-3572; Angew. Chem. Int. Ed. 2000, 39, 3428-3430.
27. S. Pritchett, D. H. Woodmansee, P. Gantzel, P. J. Walsh, J. Am. Chem. Soc. 1998, 120, 6423-6424.
28. Design and Application of Chiral Ligands for the Improvement of Metal-Catalyzed Asymmetric Transformations, C. Martin, Ph.D. thesis, MIT, 1989.
29. T. J. Davis, J. Balsells, P. Carroll, P. J. Walsh, Org. Lett. 2001, 3, 699-702.
30. D. J. Ramón, M. Yus, Tetrahedron 1998, 54, 5651-5666.
31. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
32. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
33. Y. Yamamoto, Acc. Chem. Res. 1987, 20, 243-249.
34. R. Zimmer, U. Hain, M. Berndt, R. Gewald, H. U. Reissig, Tetrahedron: Asymmetry 2000, 11, 879-887.