Preparation and transmetallation of enantioenriched α- aminoorganostannanes derived from N-boc phenylglycinol: Application to the synthesis of alafosfalin

European Journal of Organic Chemistry

Volumn , Issue 19, 2008, Pages 3344-3351

  Coeffard, Vincent ^a,b   Beaudet, Isabelle ^a,b   Evain, Michel ^a,c   Le Grognec, Erwan ^a,b   Quintard, Jean Paul ^a,b  

^a UNIVERSITÉ DE NANTES   (France)

^b Centre National de la Recherche Scientifique   (France)

^c CNRS   (France)

Author keywords

Amino acids; Asymmetric synthesis; Lithium; Tin; Transmetallation

Indexed keywords

EID: 53749093104     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800208     Document Type: Article

References (45)

1. a) D. J. Peterson, J. Organomet. Chem. 1970, 21, P63-P64;
2. b) D. J. Peterson, J. F. Ward, J. Organomet. Chem. 1974, 66, 209-217;
3. c) J.-P. Quintard, B. Elissondo, B. Jousseaume, Synthesis 1984, 495-498;
4. d) B. Elissondo, J.-B. Verlhac, J.-P. Quintard, M. Pereyre, J. Organomet. Chem. 1988, 339, 267-275.
5. R. E. Gawley, I. Coldham in The Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2004, pp 997-1053.
6. a) S. T. Kerrick, P. Beak, J. Am. Chem. Soc. 1991, 113, 9708-9710;
7. b) S. Wu, S. Lee, P. Beak, J. Am. Chem. Soc. 1996, 118, 715-721;
8. c) G. A. Weisenburger, P. Beak, J. Org. Chem. 1996, 118, 12218-12219.
9. a) J. M. Chong, S. B. Park, J. Org. Chem. 1992, 57, 2220-2222;
10. b) A. F. Burchat, J. M. Chong, S. B. Park, Tetrahedron Lett. 1993, 34, 51-54.
11. A. Ncube, S. B. Park, J. M. Chong, J. Org. Chem. 2002, 67, 3625-3636.
12. K. W. Kells, J. M. Chong, Org. Lett. 2003, 5, 4215-4218.
13. a) J.-C. Cintrat, V. Léat, J.-L. Parrain, E. Le Grognec, I. Beaudet, L. Toupet, J.-P. Quintard, Organometallics 2004, 23, 943-945;
14. b) V. Coeffard, J.-C. Cintrat, E. Le Grognec, I. Beaudet, J.-P. Quintard, J. Organomet. Chem. 2006, 691, 1488-1497.
15. a) A. P. Kaplan, P. A. Bartlett, Biochemistry 1991, 30, 8165-8170;
16. b) P. Kafarski, B. Lejczak, Phosphorus Sulfur Silicon Relat. Elem. 1991, 63, 193-215;
17. c) J. Hiratake, J. Oda, Biosci. Biotechnol. Biochem. 1997, 61, 211-218;
18. d) V. P. Kukhar, H. R. Hudson (Eds.), Aminophosphonic and Aminophosphinic Acids; John Wiley & Sons, New York, 2000.
19. For auxiliary-based synthesis of chiral α-amino phosphonic acid derivatives, see: a) B. Dhawan, D. Redmore, Phosphorus Sulfur Relat. Elem. 1987, 32, 119-144;
20. b) V. A. Kukhar, V. H. Soloshonok, V. A. Solodenko, Phosphorus Sulfur Silicon Relat. Elem. 1994, 92, 239-264;
21. c) A. B. Smith III, K. M. Yager, C. M. Taylor, J. Am. Chem. Soc. 1995, 117, 10879-10888;
22. d) K. Moonen, I. Laureyn, C. V. Stevens, Chem. Rev. 2004, 104, 6177-6215.
23. For recent reviews on catalytic asymmetric synthesis of á-amino phosphonic acid derivatives, see: e) H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948;
24. f) J.-A. Ma, Chem. Soc. Rev. 2006, 35, 630-636.
25. a) J. G. Allen, F. R. Atherton, M. J. Hall, C. H. Hassal, S. W. Holmes, R. W. Lambert, L. J. Nisbet, P. S. Ringrose, Nature 1978, 272, 56-58;
26. b) J. G. Allen, F. R. Atherton, M. J. Hall, C. H. Hassall, S. W. Holmes, R. W. Lambert, L. J. Nisbet, P. S. Ringrose, Antimicrob. Agents Chemother. 1979, 15, 684-695;
27. c) F. R. Atherton, M. J. Hall, C. H. Hassall, R. W. Lambert, W. J. Llyod, P. S. Ringrose, Antimicrob. Agents Chemother. 1979, 15, 696-705;
28. d) H. B. Maruyama, M. Arisawa, T. Sawada, Antimicrob. Agents Chemother. 1979, 16, 444-451;
29. e) F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem. 1986, 29, 29-40;
30. f) J. Neumann, M. Bruch, S. Gebauer, M. Brandsch, Eur. J. Biochem. 2004, 271, 2012-2017.
31. This coupling has already been reported by using 7 in racemic form, see: a) P. Coutrot, C. Grison, C. Charbonnier-Gérardin, Tetrahedron 1992, 48, 9841-9868;
32. b) C. Grison, C. Comoy, P. Coutrot, L'Actualité Chimique 2001, 10, 38-48.
33. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley Interscience, New York, 1999.
34. J.-C. Cintrat, V. Léat-Crest, J.-L. Parrain, E. Le Grognec, I. Beaudet, J.-P. Quintard, Eur. J. Org. Chem. 2004, 4251-4267.
35. a) J.-P. Quintard, B. Elissondo, D. Mouko-Mpegna, J. Organomet. Chem. 1983, 251, 175-187;
36. b) J. L. Parrain, I. Beaudet, J.-C. Cintrat, A. Duchêne, J.-P. Quintard, Bull. Soc. Chim. Fr. 1994, 131, 304-312.
37. The cis and trans isomers were defined by the relative position of the Bu3Sn moiety and the phenyl group on the oxazolidine cycle. See J.-C. Cintrat, V. Léat-Crest, J.-L. Parrain, E. Le Grognec, I. Beaudet, L. Toupet, J.-P. Quintard, Eur. J. Org. Chem. 2004, 4268-4279.
38. J.-C. Cintrat, E. Blart, J.-L. Parrain, J.-P. Quintard, Tetrahedron 1997, 53, 7615-7628.
39. [13]
40. V. Coeffard, E. Le Grognec, I. Beaudet, M. Lepeltier, V. Léat-Crest, J.-P. Quintard, Synthesis 2006, 24, 4151-4158.
41. F. Cavelier, C. Enjalbal, Tetrahedron Lett. 1996, 37, 5131-5134.
42. a) V. A. Solodenko, V. P. Kukhar, Tetrahedron Lett. 1989, 30, 6917-6918;
43. b) V. A. Solodenko, T. Kasheva, V. P. Kukhar, Synth. Commun. 1991, 21, 1631-1641.
44. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381-388.
45. V. Petricek, M. Dusek, L. Palatinus, JANA2006: The Crystallographic Computing System, Institute of Physics, Praha, Czech Republic, 2006.