Highly enantioselective regiodivergent and catalytic parallel kinetic resolution

Angewandte Chemie - International Edition

Volumn 40, Issue 5, 2001, Pages 930-932

  Bertozzi, Fabio ^a   Crotti, Paolo ^a   Macchia, Franco ^a   Pineschi, Mauro ^a   Feringa, Ben L ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; COPPER COMPLEX; ORGANOMETALLIC COMPOUND; PHOSPHORAMIDIC ACID;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHIRALITY; CONFORMATION; ENANTIOMER; ISOMERISM; KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0035793666     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/1521-3773(20010302)40:5<930::AID-ANIE930>3.0.CO;2-7     Document Type: Article

References (30)

1. H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249. As an alternative, the overall yield can be improved to 100 % by conducting a dynamic kinetic resolution.
2. B. A. Persson, F. F. Huerta, J. E. Bäckvall, J. Org. Chem. 1999, 64, 5237, and references therein.
3. J. Eames, Angew. Chem. 2000, 112, 913
4. Angew. Chem. Int. Ed. 2000, 39, 885.
5. E. Vedejs, X. Chen, J. Am. Chem. Soc. 1997, 119, 2584
6. F. Cardona, S. Valenza, A. Goti, A. Brandi, Eur. J. Org. Chem. 1999, 1319
7. T. M. Pedersen, J. F. Jensen, R. E. Humble, T. Rein, D. Tanner, K. Bodmann, O. Reiser, Org. Lett. 2000, 2, 535.
8. V. Alphand, R. Furstoss, J. Org. Chem. 1992, 57, 1306
9. B. Adger, M. Teresa Bes, G. Grogan, R. McCague, S. Pedragosa-Moreau, S. M. Roberts, R. Villa, P. W. H. Wan, A. J. Willetts, J. Chem. Soc. Chem. Commun. 1995, 1563
10. F. Petit, R. Furstoss, Tetrahedron: Asymmetry 1993, 4, 1341.
11. A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442
12. C. Bolm, G. Schlingloff, J. Chem. Soc. Chem. Commun. 1995, 1247.
13. M. P. Doyle, A. B. Dyatkin, A. V. Kalinin, Q. A. Ruppar, S. F. Martin, M. R. Spaller, S. Liras, J. Am. Chem. Soc. 1995, 117, 11021.
14. F. Badalassi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Tetrahedron Lett. 1998, 39, 7795
15. F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Org. Lett. 2000, 2, 933; for an overview of phosphoramidite in catalytic asymmetric conjugate addition
16. B. L. Feringa, Acc. Chem. Res. 2000, 33, 346
17. R. Naasz, L. A. Arnold, B. L. Feringa, Angew. Chem. 2001, 113, 956
18. Angew. Chem. Int. Ed. 2001, 40, 927.
19. H. Kagan, Croat. Chem. Acta 1996, 69, 669.
20. N. Krause, A. Gerold, Angew. Chem. 1997, 109, 194
21. Angew. Chem. Int. Ed. Engl. 1997, 36, 187.
22. C. Ullenius, B. Christenson, Pure Appl. Chem. 1988, 60, 57
23. E. J. Corey, N. W. Boaz, Tetrahedron Lett. 1985, 26, 6015
24. N. Krause, R. Wagner, A. Gerold, J. Am. Chem. Soc. 1994, 116, 381
25. J. P. Snyder, Angew. Chem. 1995, 107, 80
26. Angew. Chem. Int. Ed. Engl. 1995, 34, 80.
27. E. S. M. Persson, M. van Klaveren, D. M. Grove, J. E. Bäckvall, G. van Koten, Chem. Eur. J. 1995, 1, 351. Even if not indicated for the sake of simplicity in Scheme 2, the copper(iii) complexes 3B, D and 4B, D are probably cationic species with TfO as a possible counterion.
28. E. Nakamura, M. Yamanaka, S. Mori, J. Am. Chem. Soc. 2000, 122, 1826
29. D. E. Frantz, D. A. Singleton, J. P. Snyder, J. Am. Chem. Soc. 1997, 119, 3383.
30. M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837.