Enantioselective synthesis of (+)(R)- And (-)(S)-nicotine based on Ir-catalysed allylic amination

Organic and Biomolecular Chemistry

Volumn 3, Issue 18, 2005, Pages 3266-3268

  Welter, Carolin ^a   Moreno, Rosa M ^a   Streiff, Stephane ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSIS; CHEMICAL BONDS; SYNTHESIS (CHEMICAL);

ALLYL AMINATION; BOND REDUCTIONS; ENANTIOSELECTIVE SYNTHESIS; METATHESIS;

IRIDIUM;

EID: 26444554565     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508634e     Document Type: Article

References (28)

1. J. A. Rosecrans, Chem. Ind. (London), 1998, 525;
2. M. W. Holladay, M. J. Dart and J. K. Lynch, J. Med. Chem., 1997, 40, 4769.
3. Reviews: F.-X. Felpin and A. Lebreton, Eur. J. Org. Chem., 2003, 3693;
4. I. R. Baxendale, G. Brusotti, M. Matsuoka and S. V. Ley, J. Chem. Soc., Perkin Trans, 1, 2002, 143.
5. R. Stragies and S. Blechert, J. Am. Chem. Soc., 2000, 122, 9584;
6. H. Ovaa, R. Strategies, G. A. van der Marel, J. H. van Boom and S. Blechert, Chem. Commun., 2000, 1501.
7. P. A. Evans and J. E. Robinson, Org. Lett., 1999, 1, 1929.
8. F.-X. Felpin, S. Girard, G. Vo-Thanh, R. J. Robins, J. Villiéras and J. Lebreton, J. Org. Chem., 2001, 66, 6305.
9. G. Lipowsky and G. Helmchen, Chem. Commun, 2004, 116;
10. C. A. Kiener, C. Shu, C. Incarvito and J. F. Hartwig, J. Am. Chem. Soc, 2003, 125, 14272;
11. H. Miyabe, K. Yoshida, Y. Kobayashi, A. Matsumura and Y. Takemoto, Synlett, 2003, 1031;
12. R. Takeuchi, Synlett, 2002, 1954;
13. K. Tissot-Croset, D. Polet and A. Alexakis, Angew. Chem., Int. Ed., 2004, 43, 2426;
14. A. Leitner, C. Shu and J. F. Hartwig, Proc. Natl. Acad. Sci., 2004, 101, 5830.
15. (a) C. Welter, A. Dahnz, B. Brunner, S. Streiff, P. Dübon and G. Helmchen, Org. Lett, 2005, 7, 1239;
16. (b) C. Welter, O. Koch, G. Lipowsky and G. Helmchen, Chem. Commun., 2004, 896.
17. B. Feringa, Acc. Chem. Res., 2000, 33, 346.
18. K. Tissot-Croset, D. Polet, S. Gille, C. Hawner and A. Alexakis, Synthesis, 2004, 2586.
19. It is important to note that the reaction must be run in the presence of dry air; under inert gas the inhibitor is not active.
20. In contrast, the formation of the N-formyl derivative of 2a by reaction with DCC and formic acid proceeded without polymerisation in 85% yield.
21. M. Scholl, T. M. Trnka, J. P. Morgan and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 2247.
22. Concerning racemisation in the catalytic hydrogenation of dehydronicotine, cf.: C. D. Chavdarian, J. Org. Chem, 1983, 48, 1529.
23. E. Montenegro, B. Gabler, G. Paradies, M. Seemann and G. Helmchen, Angew. Chem., Int. Ed., 2003, 42, 2419;
24. D. J. Pasto and R. T. Taylor, Org. React., 1991, 40, 91.
25. R[(R)-6] = 24.1 min. Ee values found for nicotine were equal to those of the precursor 2a: 96% ee for (R)-6 and 99% ee for (S)-6 obtained from 2a, which was prepared according to entry 2 and entry 3, respectively, of Table 1.
26. Benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-yl)(tricyclohexyl- phosphino)ruthenate; prepared according to: S. B. Garber, J. S. Kingsbury, B. L. Gray and A. Hoveyda, J. Am. Chem. Soc., 2000, 122, 8168.
27. Signals of a ca. 1 : 1 mixture of amide rotamers.
28. W. Windus and C. S. Marvel, J. Am. Chem. Soc., 1930, 52, 2543.