Synthesis of 1-aminocyclopropyl-pentanoic and - heptanoic acid derivatives

Letters in Organic Chemistry

Volumn 5, Issue 5, 2008, Pages 328-331

  Gensini, Martina ^a   Quartara, Laura ^a   Altamura, Maria ^a  

^a Dipartimento di Chimica   (Italy)

Author keywords

Amides; Amines; Cyclopropanation; Grignard reagent; Titanium

Indexed keywords

EID: 50349088272     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808784872034     Document Type: Article

References (29)

1. a) Liu, H.-W.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group, Rappoport, Z. Ed.: Wiley 1987; 959;
2. b) Salaiin, J. Top. Curr. Chem. 2000, 207, 1;
3. c) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev., 2003, 103, 1625.
4. a) Brighty, K. E.; Castaldi, M. J. Synlett, 1996, 1097;
5. b) Högberg, M.; Sahlberg, C.; Engelhardt, P.; Noréen, R.; Kangasmetsä, J.; Johansson, N. G.; Öberg, B.; Vrang, L.; Zhang, H.; Sahlberg, B.-L.; Unge, T.; Lövgren, S.; Fridborg, K.; Bäckbro, K. J. Med. Chem., 1999, 42, 4150.
6. Donaldson, W. A. Tetrahedron, 2001, 57, 8589.
7. (a) Chaplinski, V.; de Meijere, A. Angew. Chem., 1996, 108, 491;
8. Angew. Chem. Int. Ed. Engl., 1996, 35, 413;
9. (b) Chaplinski, V.; Winsel, H.; Kordes, M.; de Meijere, A. Synlett, 1997, 111.
10. a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A.; Prityskaya, T. S. Zh. Org. Khim., 1989, 25, 2244;
11. J. Org. Chem. USSR, 1990, 25, 2027;
12. Zh. Org. Khim., 1991, 27, 294;
13. J. Org. Chem. USSR, 1991, 27, 250;
14. b) Kulinkovich, O. G.; Vasilevski, D. A.; Savchenko, A. I.; Sviridov, S. V. J. Org. Chem. USSR, 1992, 27, 1249;
15. c) Kulinkovich, O. G. Chem. Rev., 2003, 103, 2597.
16. For reviews see: a) Kulinkovich, O. G.; de Meijere, A. Chem. Rev., 2000, 100, 2789.
17. b) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A.I. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; 390.
18. c) Brackmann, F.; de Meijere, A. Chem. Rev., 2007, 107, 4493;
19. Chem. Rev., 2007, 107, 4538.
20. For the synthesis of GABA analogs see: Kordes, M.; Winsel, H.; de Meijere, A. Eur. J. Org. Chem., 2000, 3235.
21. Francowski, A.; Deredas, D.; Dubost, E.; Gessier, F.; Jankowski, S.; Neuburger, M.; Seliga, C.; Tschamber, T.; Weinberg, K. Tetrahedron, 2003, 59, 6503.
22. Gensini, M.; de Meijere, A. Chem. Eur. J., 2004, 10, 785.
23. 3 solution and dried. After removal of the solvent the crude oil was purified by flash chromatography.
24. + -Bn].
25. Xu, H.; Kinsel, G. R.; Zhang, J.; Li, M.; Rudchevich, D. M. Tetrahedron, 2003, 59, 5837.
26. For the tbutyl ester preparation see: Takeda, K.; Akiyama, A.; Nakamura, H.; Takizawa, S.; Mizuno, Y.; Takayanagi, H.; Harigaya, Y. Synthesis, 1994, 1063.
27. +-Bn].
28. Willson, F. G.; Wheeler, T. S. Org. Synth., Coll. 1941; Vol. I, p. 102; Ann. 1928; Vol. 8, p. 38.
29. +.