Convenient Route to 2-(Trialkylstannyl)cyclopropylamines and Their Application in Palladium-Catalyzed Cross-Coupling Reactions

European Journal of Organic Chemistry

Volumn , Issue 3, 2004, Pages 631-635

  Wiedemann, Stefan ^a   Rauch, Karsten ^a   Savchenko, Andrei ^a   Marek, Ilan ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Cross coupling; Rearrangement; Small ring systems; Tin; Titanium

Indexed keywords

5 (DIBENZYLAMINO)CYCLOPENT 2 ENECARBOXYLATE; ACRYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLAMINE DERIVATIVE; ETHYL 3 IODOACRYLATE; FORMAMIDE DERIVATIVE; IODIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPYLAMINE; TIN DERIVATIVE; TITANIUM; TRIBUTYLVINYLSTANNANE; UNCLASSIFIED DRUG;

AMINOCYCLOPROPANATION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLOPROPANATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STILLE REACTION; SYNTHESIS;

EID: 1242308377     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300454     Document Type: Article

References (21)

1. [1a] J. Salaün, M. S. Baird, Curr. Med. Chem. 1995, 2, 511-542.
2. [1b] j. Salaün, Top. Curr. Chem. 2000, 207, 1-67.
3. Cf. foonote (1) in: M. L. Gillaspy, B. A. Lefker, W. A. Hada, D. J. Hoover, Tetrahedron Lett. 1995, 36, 7399-7402.
4. A. de Meijere, V. Chaplinski, F. Gerson, P. Merstetter, E. Haselbach, J. Org. Chem. 1999, 64, 6951-6959.
5. A. de Meijere, S. I. Kozhushkov, A. I. Savchenko, in Titanium and Zirconium in Organic Synthesis (Ed.: I. Marek), Wiley-VCH, Weinheim, 2002, pp. 390-434.
6. Review: O. G. Kulinkovich, A. de Meijere, Chem. Rev. 2000, 100, 2789-2834.
7. A. de Meijere, C. M. Williams, A. Kourdioukov, S. V. Sviridov, V. Chaplinski, M. Kordes, A. I. Savchenko, C. Stratmann, M. Noltemeyer, Chem. Eur. J. 2002, 8, 3789-3801.
8. I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063-2192.
9. For the use of vinylstannanes in the synthesis of vinylcyclopropanols see: K. Lee, S. Kim, J. K. Cha, J. Org. Chem. 1998, 63, 9135-9138.
10. V. Launay, I. Beaudet, J.-P. Quintard, Synlett 1997, 821-823.
11. R. Mizojiri, H. Urabe, F. Sato, J. Org. Chem. 2000, 65, 6217-6222.
12. T. Itoh, S. Emoto, M. Kondo, Tetrahedron 1998, 54, 5225-5232.
13. M. Pohmakotr, A. Takampon, Tetrahedron Lett. 1996, 37, 4585-4588.
14. M. Lautens, P. H. M. Delanghe, J. B. Goh, C. H. Zhang, J. Org. Chem. 1995, 60, 4213-4227.
15. [14a] E. Piers, M. Jean, P. S. Marrs, Tetrahedron Lett. 1987, 28, 5075-5078.
16. [14b] E. Piers, J. Banville, C. K. Lau, I. Nagakura, Canad. J. Chem. 1982, 60, 2965-2975.
17. D. Peters, A. B. Hörnfeldt, S. Gronowitz, J. Heterocycl. Chem. 1991, 28, 1629-1631.
18. W. D. Schmitz, D. Romo, Tetrahedron Lett. 1996, 37, 4857-4860.
19. V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905-5911.
20. Reviews see: [18a] H.-U. Reißig, Topics Curr. Chem. 1988, 144, 73-135.
21. [18b] H.-U. Reißig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196.