Cobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: Synthesis of enantiomerically enriched atropoisomers of 2-arylpyridines

Angewandte Chemie - International Edition

Volumn 43, Issue 29, 2004, Pages 3795-3797

  Gutnov, Andrey ^a   Heller, Barbara ^a   Fischer, Christine ^a   Drexler, Hans Joachim ^a   Spannenberg, Anke ^a   Sundermann, Bernd ^b   Sundermann, Corinna ^b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b GRÜNENTHAL GMBH   (Germany)

Author keywords

Asymmetric catalysis; Atropoisomerism; Cobalt; Cyclotrimerization; Nitrogen heterocycles

Indexed keywords

ACETYLENE; ADDITION REACTIONS; CATALYSTS; COBALT; ISOMERS;

ATROPOSISOMERS; CHIRAL INDUCTION; CYCLOADDITION; NITRILES;

CATALYSIS;

ALKYNE DERIVATIVE; COBALT; NITRILE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CYCLOADDITION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 4544286694     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454164     Document Type: Article

References (32)

1. a) K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525-628; Angew. Chem. Int. Ed. Engl. 1984, 23, 539-556;
2. a) K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525-628; Angew. Chem. Int. Ed. Engl. 1984, 23, 539-556;
3. b) H. Bönnemann, Angew. Chem. 1985, 97, 264-279; Angew. Chem. Int. Ed. Engl. 1985, 24, 248;
4. b) H. Bönnemann, Angew. Chem. 1985, 97, 264-279; Angew. Chem. Int. Ed. Engl. 1985, 24, 248;
5. c) N. E. Schore, Chem. Rev. 1988, 88, 1081-1119;
6. d) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1129-1162;
7. e) D. B. Grotjahn in Comprehensive Organometallic Chemistry II, Vol. 12 (Ed.: L. S. Hegedus), Pergamon, Oxford, 1995, pp. 741-770;
8. f) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92;
9. g) S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901-2915;
10. h) J. A. Varela, C. Saá, Chem. Rev. 2003, 103, 3787-3801.
11. Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135.
12. a) I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, Š. Vyskočil, D. Šaman, Tetrahedron Lett. 1999, 40, 1993-1996;
13. b) F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Šaman, Š. Vyskočil, P. Fiedler, J. Org. Chem. 2003, 68, 5193-5197.
14. a) B. Heller, G. Oehme, J. Chem. Soc. Chem. Commun. 1995, 179-180;
15. b) B. Heller, D. Heller, G. Oehme, J. Mol. Catal. A 1996, 110, 211-219;
16. c) B. Heller, B. Sundermann, H. Buschmann, H.-J. Drexler, J. You, U. Holzgrabe, E. Heller, G. Oehme, J. Org. Chem. 2002, 67, 4414-4422;
17. d) B. Heller, B. Sundermann, C. Fischer, J. You, W. Chen, H.-J. Drexler, P. Knochel, W. Bonrath, A. Gutnov, J. Org. Chem. 2003, 68, 9221-9225.
18. a) N. W. Alcock, J. M. Brown, D. I. Hulmes, Tetrahedron: Asymmetry 1993, 4, 743-756;
19. b) R. W. Baker, S. O. Rea, M. V. Sargent, E. M. C. Schenkelaars, B. W. Skelton, A. H. White, Tetrahedron: Asymmetry 1994, 5, 45-48;
20. c) X. C. Wang, H. N. C. Wong, Tetrahedron 1995, 51, 6941-6960;
21. d) G. Chelucci, M. A. Cabras, A. Saba, A. Sechi, Tetrahedron: Asymmetry 1996, 7, 1027-1032;
22. e) H. Zhang, F. Xue, T. C. W. Mak, K. C. Chan, J. Org. Chem. 1996, 61, 8002-8003;
23. f) G. Chelucci, A. Bacchi, D. Fabbri, A. Saba, F. Ulgheri, Tetrahedron Lett. 1999, 40, 553-556;
24. g) H. Brunner, G. Olschewski, B. Nuber, Synthesis 1999, 3, 429-434;
25. h) H. L. Wong, Y. Tian, K. S. Chan, Tetrahedron Lett. 2000, 41, 7723-7726;
26. i) S. C. Tucker, J. M. Brown, J. Oakes, D. Thornthwaite, Tetrahedron 2001, 57, 2545-2554;
27. j) T. Shimada, A. Kina, S. Ikeda, T. Hayashi, Org. Lett. 2002, 4, 2799-2801;
28. k) A. V. Malkov, L. Dufková, L. Farrugia, P. Koč ovský, Angew. Chem. 2003, 115, 3802-3805; Angew. Chem. Int. Ed. 2003, 42, 3674-3677.
29. k) A. V. Malkov, L. Dufková, L. Farrugia, P. Koč ovský, Angew. Chem. 2003, 115, 3802-3805; Angew. Chem. Int. Ed. 2003, 42, 3674-3677.
30. a) A. Gutnov, B. Heller, H.-J. Drexler, A. Spannenberg, G. Oehme, Organometallics 2003, 22, 1550-1553;
31. b) A. Gutnov, H.-J. Drexler, A. Spannenberg, G. Oehme, B. Heller, Organometallics 2004, 23, 1002-1009.
32. X-ray data and experimental procedures are given in Supporting Information. CCDC-232659 (20) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).