Copper(I)-catalyzed enantioselective substitution of allyl chlorides with diorganozinc compounds

Angewandte Chemie - International Edition

Volumn 38, Issue 3, 1999, Pages 379-381

  Dübner, Frank ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Asymmetric catalysis; Copper; Ferrocenes; Substitutions

Indexed keywords

ALLYL CHLORIDE; COPPER; FERROCENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS;

EID: 0042368347     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO;2-Y     Document Type: Article

References (21)

1. a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
2. b) O. Reiser, Angew. Chem. 1993, 105, 576; Angew. Chem. Int. Ed. Engl. 1993, 32, 547.
3. b) O. Reiser, Angew. Chem. 1993, 105, 576; Angew. Chem. Int. Ed. Engl. 1993, 32, 547.
4. a) T. Hayashi, M. Kawatasura, Y. Kozumi, Chem. Commun. 1997, 562;
5. b) J. P. Janssen, G. Helmchen, Tetrahedron Lett. 1997, 38, 8025;
6. c) R. Pretôt, A. Pfaltz, Angew. Chem. 1998, 110, 337; Angew. Chem. Int. Ed. 1998, 37, 323;
7. c) R. Pretôt, A. Pfaltz, Angew. Chem. 1998, 110, 337; Angew. Chem. Int. Ed. 1998, 37, 323;
8. d) B. M. Trost, I. Hachiya, J. Am. Chem. Soc. 1998, 120, 1104.
9. a) A. Commercon, M. Bourgain, M. Delaumeny, J. F. Normant, J. Villieras, Tetrahedron Lett. 1975, 3837;
10. b) P. Barsantai, V. Calo, L. Lopez, G. Marchese, F. Naso, G. Pesce, J. Chem. Soc. Chem. Commun. 1978, 1085;
11. c) C. C. Tseng, S. D. Paisley, H. L. Goering, J. Org. Chem. 1986, 51, 2884;
12. d) J.-F. Bäckvall, M. Sellen, B. Grant, J. Am. Chem. Soc. 1990, 112, 6615;
13. e) J.-E. Bäckvall, E. S. M. Persson, A. Bombrun, J. Org. Chem. 1994, 59, 4126;
14. f) E. S. M. Persson, M. van Klaveren, D.M. Grove, J.-E. Bäckvall, G. van Koten, Chem. Eur. J. 1995. 1, 351.
15. The best enantioselectivity for a copper(1)-catalyzed allylation is 42% ee: M. van Klaveren, E. S. M. Persson, A. del Villar, D. M. Grove, J.-E. Bäckvall, G. van Koten, Tetrahedron Lett. 1995, 36, 3059.
16. L. Schwink, P. Knochel, Chem. Eur. J. 1998, 4, 950.
17. F. Langer, L. Schwink, A. Devasagayaraj, P.-Y. Chavant, P. Knochel, J. Org. Chem. 1996, 61, 8229.
18. R. Köster, G. Griasnow, W. Larbig, P. Binger, Justus Liebigs Ann. Chem. 1964, 672, 1.
19. A patent with Zeneca Ltd. has been filed.
20. The absolute configuration of the products 4 was determined by analogy with the literature: a) L. Lardicci, P. Salvadori, A. M. Caporusso, R. Menicagli, E. Belgodere, Gazz. Chim. Ital. 1972, 102. 64;
21. b) L. Lardicci, R. Menicagli, P. Salvadori, Gazz. Chim. Ital. 1968, 98, 738.