The formation of a crystalline oxazolidin-5-one from (L)-alanine and its use as a chiral template in the practical synthesis of α-substituted alanine esters

Chimia

Volumn 60, Issue 9, 2006, Pages 566-573

  Eriksson, Magnus ^a   Napolitano, Elio ^a   Xu, Jinghua ^a   Kapadia, Suresh ^a   Byrne, Denis ^a   Nummy, Laurence ^a   Grinberg, Nelu ^a   Shen, Sherri ^a   Lee, Heewon ^a   Farina, Vittorio ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

Crystallization induced asymmetric transformation; Diastereoselective alkylation; Oxazolidin 5 one; , Disubstituted amino acid

Indexed keywords

EID: 33749854297     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2006.566     Document Type: Article

References (40)

1. a) R.M. Williams, 'Synthesis of Optically Active α-Amino Acids', Organic Chemistry Series, Vol. 7, Eds. J.E. Baldwin, P.D. Magnus, Pergamon Press, Oxford 1989;
2. b) H. Heimgartner, Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264.
3. K. Last-Barney, W. Davidson, M. Cardozo, L.L. Frye, C. A. Grygon, J.L. Hopkins, D.D. Jeanfavre, S. Pav, C. Qian, J.M. Stevenson, L. Tong, R. Zindell, T.A. Kelly, J. Am. Chem. Soc. 2001, 123, 5643-5650.
4. T.A. Kelly, D.D. Jeanfavre, D.W. McNeil, J. Woska, P.L. Reilly, E.A. Mainolfi, K.M. Kishimoto, G.H. Nabozny, R. Zinter, B.J. Bormann, R.J. Rothlein, Immunol. 1999, 163, 5173.
5. a) C. Cativiela, M.D. Diaz-de-Villegas, Tetrahedron Asymmetry 1998, 9, 3517-3599;
6. b) R.O. Duthaler, Tetrahedron 1994, 50, 1539-1650;
7. c) T. Wirth, Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
8. a) U. Schöllkopf, W. Hartwig, U. Groth, K.-O. Westphalen, Liebigs Ann. Chem. 1981, 696;
9. b) U. Schöllkopf, U. Groth, K.-O. Westphalen, C. Deng, Synthesis 1981, 969-971.
10. c) U. Schöllkopf, Tetrahedron 1983, 39, 2085-2091 and references cited therein.
11. See also J. Chen, S.P. Corbin, N.J. Holman, Org. Process Res. Dev. 2005, 9, 185-187.
12. a) R.M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286;
13. b) R.M. Williams, M.-N. Im, Tetrahedron Lett. 1988, 29, 6075-6078;
14. c) P.J. Sinclair, D. Zhai, J. Reibenspies, R.M. Williams, J. Am. Chem. Soc. 1986, 108, 1103-1104;
15. d) R.M. Williams, in 'Advances in Asymmetric Synthesis', Ed. A. Hassner, JAI Press, Greenwich, CT, 1995; Vol 1, pp 45-94 and references cited therein.
16. a) D. Seebach, A. Fadel, Helv. Chim. Acta 1985, 68, 1243-1250;
17. b) R. Naef, D. Seebach, Helv. Chim. Acta 1985, 68, 135-143.
18. D. Seebach, A.R. Sting, M. Hoffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748 and references cited therein.
19. N. Yee, Org. Lett. 2000, 2, 2781-2783.
20. R.P. Frutos, S. Stehle, L. Nummy, N. Yee, Tetrahedron Asymmetry 2001, 12, 101-104.
21. N. Yee, L.J. Nummy, R.P. Frutos, J.J. Song, E. Napolitano, D.P. Byrne, P.-J. Jones, V. Farina, Tetrahedron Asymmetry 2003, 14, 3495-3501.
22. S.R. Kapadia, D.M. Spero, M. Eriksson, J. Org. Chem. 2001, 66, 1903-1905.
23. E. Napolitano, V. Farina, Tetrahedron Lett. 2001, 42, 3231-3234.
24. A. Fadel, J. Salaün, Tetrahedron Lett. 1987, 28, 2243-2246.
25. E. Altmann, K. Nebel, M. Mutter, Helv. Chim. Acta 1991, 74, 800-806.
26. K. Nebel, M. Mutter, Tetrahedron 1988, 44, 4793-4796.
27. A. Alonso, S.G. Davis, A.S. Elend, J.L. Haggit, J. Chem. Soc., Perkin Trans. 1 1998, 257-264.
28. S. Karady, J.S. Amato, L.M. Weinstock, Tetrahedron Lett. 1984, 23, 4337-4340.
29. H. Cheng, P. Keitz, J.B. Jones, J. Org. Chem. 1994, 59, 7671-7676.
30. W.D. Shrader, C.K. Marlowe, Bioorg. & Med. Chem. Lett. 1995, 5, 2207-2210.
31. F. Micheel, W. Meckstroth, Chem. Ber. 1959, 92, 1675-1679.
32. N.G. Anderson, Org. Process Res. Dev. 2005, 9, 800-813 and references therein.
33. M. Neuenschwander, P. Bigler, K. Christen, R. Isell, R. Kyburz, H. Mühle, Helv. Chim. Acta 1978, 61, 2047-2058.
34. T.F. Buckley III, H. Rapoport, J. Am. Chem. Soc. 1981, 103, 6157-6160.
35. J.H. Jones, M.J. Witty, J. Chem. Soc., Perkin Trans. 1 1979, 3203-3206.
36. R.W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
37. Only one peak is observed although 16 should be present as two diastereomers. It is possible that the two signals overlap given the closeness of the signals from C(2) in cis- and trans-15c. [28] This material is commercially available on metric ton scale for less than $50/kg. In comparison, the price for research amounts is about $10/g.
38. D.P. Kjell, B.J. Slattery, M.J. Semo, J. Org. Chem. 1999, 64, 5722-5724.
39. Only 33% yield over two steps was obtained in the absence of DMPU.
40. R.A. Aitken, N. Karodia, T. Massil, R.J. Young, J. Chem. Soc., Perkin Trans. 1 2002, 533-541.