A highly enantioselective catalyst for the asymmetric Nozaki-Hiyama-Kishi reaction of allylic and vinylic halides

Angewandte Chemie - International Edition

Volumn 42, Issue 9, 2003, Pages 1032-1035

  Berkessel, Albrecht ^a   Menche, Dirk ^a   Sklorz, Christoph A ^a   Schröder, Michael ^a   Paterson, Ian ^b  

^a UNIVERSITY OF COLOGNE   (Germany)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Asymmetric catalysis; Chromium; Manganese; N,O ligands; Schiff bases

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; STEREOCHEMISTRY;

ENANTIOSELECTIVE CATALYSTS; STEREOINDUCTION;

CATALYSTS;

ALDEHYDE DERIVATIVE; ALLYL COMPOUND; BENZYL DERIVATIVE; BORNANE DERIVATIVE; HALIDE; LIGAND; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0037416337     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390265     Document Type: Article

References (37)

1. For reviews, see: a) A. S. K. Hashmi, J. Prakt. Chem. 1996, 338, 491-495;
2. b) L. A. Wessjohann, G. Scheid, Synthesis 1999, 1-36;
3. b) A. Fürstner, Chem. Rev. 1999, 99, 991-1045;
4. c) A. Fürstner, Chem. Eur. J. 1998, 4, 567-570.
5. A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 12349-12357.
6. a) C. Chen, K. Tagami, Y. Kishi, J. Org. Chem. 1995, 60, 5386-5387;
7. b) Y. Kishi, Tetrahedron 2002, 58, 6239-6258;
8. c) H. S. Schrekker, M. W. G. de Bolster, R. V. A. Orru, L. A. Wessjohann, J. Org. Chem. 2002, 67, 1975-1981.
9. For asymmetric versions of the NHK reaction using stoichiometric amounts of chiral organochromium agents, see: a) B. Cazes, C. Verniere, J. Goré, Synth. Commun. 1983, 13, 73-79; b) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 1997, 62, 2322-2323; and ref. [3a].
10. For asymmetric versions of the NHK reaction using stoichiometric amounts of chiral organochromium agents, see: a) B. Cazes, C. Verniere, J. Goré, Synth. Commun. 1983, 13, 73-79; b) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 1997, 62, 2322-2323; and ref. [3a].
11. a) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi, Angew. Chem. 1999, 111, 3558-3561; Angew. Chem. Int. Ed. 1999, 38, 3357-3359;
12. a) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi, Angew. Chem. 1999, 111, 3558-3561; Angew. Chem. Int. Ed. 1999, 38, 3357-3359;
13. b) M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Polyhedron 2000, 19, 537-539;
14. c) M. Bandini, P G. Cozzi, A. Umani-Ronchi, Angew. Chem. 2000, 112, 2417-2420; Angew. Chem. Int. Ed. 2000, 39, 2327-2330;
15. c) M. Bandini, P G. Cozzi, A. Umani-Ronchi, Angew. Chem. 2000, 112, 2417-2420; Angew. Chem. Int. Ed. 2000, 39, 2327-2330;
16. d) M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Tetrahedron 2001, 57, 835-843;
17. e) M. Bandini, P. G. Cozzi, P. Melchiorre, S. Morganti, A. Umani-Ronchi, Org. Lett. 2001, 3, 1153-1155;
18. f) After submission of this manuscript, a report by Kishi et al. on a catalytic enantioselective process using an oxazoline sulfonamide ligand appeared: H.-W. Choi, K. Nakajima, D. Demeke, F.-A. Kang, H.-S. Jun, Z.-K. Wan, Y. Kishi, Org. Lett. 2002, 4, 4435-4438. However, the enantioselectivities reported are not as high as our best examples.
19. For a review of applications of Cr-salen complexes in asymmetric catalysis, see: M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Chem. Commun. 2002, 919-927.
20. For two examples, see: a) X.-G. Zhou, J.-S. Huang, X.-Q. Yu, Z.-Y. Zhou, C.-M. Che, J. Chem. Soc. Dalton Trans. 2000, 1075-1080;
21. b) D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. 2001, 113, 96-142; Angew. Chem. Int. Ed. 2001, 40, 92-138.
22. b) D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. 2001, 113, 96-142; Angew. Chem. Int. Ed. 2001, 40, 92-138.
23. a) T. Hayashi, Acta Chem. Scand. 1996, 50, 259-266;
24. b) A. Weissfloch, R. Azerad, Bioorg. Med. Chem. 1994, 2, 493-5000.
25. R. T. Hawkins, R. S. Hsu, S. G. Wood, J. Org. Chem. 1978, 43, 4648-4650.
26. A full account of the synthesis and configurational assignment of (+)- and (-)-DIANANE (9) will be published elsewhere.
27. K. Ishihara, M. Mouri, Q. Gao, T Maruyama, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 11490-11495.
28. A. B. Smith III, K. P. Minibiole, P. R. Verhoest, M. Schelhaas, J. Am. Chem. Soc. 2001, 123, 10942-10953.
29. V. K. Tandon, A. M. van Leusen, H. Wynberg, J. Org. Chem. 1983, 48, 2767-2769.
30. Y. Wu, L. Esser, J. K. De Brabander, Angew. Chem. 2000, 112, 4478-4480; Angew. Chem. Int. Ed. 2000, 39, 4308-4310.
31. Y. Wu, L. Esser, J. K. De Brabander, Angew. Chem. 2000, 112, 4478-4480; Angew. Chem. Int. Ed. 2000, 39, 4308-4310.
32. The synthesis of the aldehyde was performed according to: a) M. J. Martinelli, J. Org. Chem. 1990, 55, 5065-5073; b) T. Oka, A. Murai, Tetrahedron 1998, 54, 1-20.
33. The synthesis of the aldehyde was performed according to: a) M. J. Martinelli, J. Org. Chem. 1990, 55, 5065-5073; b) T. Oka, A. Murai, Tetrahedron 1998, 54, 1-20.
34. The possibility to recover the valuable ligand by column chromatography after aqueous work-up further adds to the efficiency of our process. Usually, at least 80 % of ligand could be recovered in pure form.
35. J. K. Stille, J. H. Simpson, J. Am. Chem. Soc. 1987, 109, 2138-2152.
36. K. Takai, K. Sakogawa, Y. Kataoka, K. Oshima, K. Utimoto, Org. Synth. 1995, 72, 180-188.
37. 2 were added prior to the halide.