An efficient synthesis of (R)-2-Butyl-3-hydroxypropionic acid

Organic Process Research and Development

Volumn 11, Issue 1, 2007, Pages 90-93

  Bin, Hu ^a   Prashad, Mahavir ^a   Har, Denis ^a   Prasad, Kapa ^a   Repič, Oljan ^a   Blacklock, Thomas J ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847719189     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op060199l     Document Type: Article

References (32)

1. (a) Jiang, X.; Prasad, K.; Prashad, M.; Slade, J.; Repic, O.; Blacklock, T. J. Synlett 2006, 3179-3181.
2. (b) Slade, J.; Parker, D.; Girgis, M.; Mueller, M.; Vivelo, J.; Liu, H.; Bajwa, J.; Chen, G. P.; Carosi, J.; Lee, P.; Chaudhary, A.; Wambser, D.; Prasad, K.; Bracken, K.; Dean, K.; Boehnke, H.; Repic, O.; Blacklock, T. J. Org. Process Res. Dev. 2006, 10, 78-93.
3. Sakai, N.; Ageishi, S.; Isobe, H.; Hayashi, Y.; Yamamoto, Y J. Chem. Soc., Perkin Trans. J 2000, 71-77.
4. Green, F. R.; Goodhue, C. T.; Olyslager, R. J. EP0354529, February 2, 1990.
5. Schneider, M.; Engel, N.; Boensmann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 66.
6. (a) Canet, J. L.; Fadel, A.; Salaun, J. J. Org. Chem. 1992, 57, 3463-3473.
7. (b) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211-12216.
8. (c) Honda, T.; Ogino, T. Tetrahedron: Asymmetry 1998, 9, 2663-2669.
9. (d) Fadel, A.; Vandromme, L. Tetrahedron: Asymmetry 1999, 10, 1153-1162.
10. (e) Arzel, P.; Freida, V.; Weber, P.; Fadel, A. Tetrahedron: Asymmetry 1999, 10, 3877-3881.
11. De Jeso, B.; Belair, N.; Deleuze, H.; Rascle, M. C.; Maillard, B. Tetrahedron Lett. 1990, 31, 653-654.
12. Klotz-Berendes, B.; Kleemis, W.; Jegelka, U.; Schafer, H. J.; Kotila, S. Tetrahedron: Asymmetry 1997, 8, 1821-1823.
13. (a) Pfeffer, P. E.; Kinsel, E.; Silbert, L. S. J. Org. Chem. 1972, 37, 1256-1258.
14. (b) Pfeffer, P. E.; Silbert, L. S. U.S. Patent 3,912,772, October 14, 1975.
15. (c) Ho, W.; Tutwiler, G. F.; Cottrell, S. C.; Morgans, D. J.; Tarhan, O.; Mohrbacher, R. J. J. Med. Chem. 1986, 29, 2184-2190.
16. (a) Ayers, T. A. Tetrahedron Lett. 1999, 40, 5467-5470.
17. (b) Ayers, T. A.; Brown, P. W. U.S. Patent 6,407,119, June 18, 2002.
18. (a) Livermore, D. G. H.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. I 1982, 1019-1023.
19. (b) Dubois, J.; Foures, C.; Bory, S.; Falcou, S.; Gaudry, M.; Marquet, A. Tetrahedron 1991, 47, 1001-1012.
20. (c) Byun, H. S.; Reddy, K. C.; Bittman, R. Tetrahedron Lett. 1994, 35, 1371-1374.
21. (d) Welch, K. N. J. Chem. Soc. 1930, 257-261.
22. (e) Villieras, J.; Rambaud, M. Synthesis 1982, 924-926.
23. (a) Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429-2433.
24. (b) Ghosh, S.; Pardo, S. N.; Salomon, R. G. J. Org. Chem. 1982, 47, 4692-4702.
25. (a) Stetter, H.; Kuhlmann, H. Synthesis 1979, 29-30.
26. (b) Ho, W.; Tutwiler, G. F.; Cottrell, S. C.; Morgans, D. J.; Tarhan, O.; Mohrbacher, R. J. J. Med. Chem. 1986, 29, 2184-2190.
27. (c) Cason, J.; Kalm, M. J.; Mills, R. H. J. Org. Chem. 1953, 18, 1670-1674.
28. (a) Prashad, M.; Har, D.; Kim, H. Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067-7070.
29. (b) Bianco, A.; Passacantilli, P.; Righi, G. Synth. Commun. 1988, 18, 1765-1771.
30. (a) Patel, D.; Ryono, D. E. Bioorg. Med. Chem. Lett. 1992, 2, 1089-1092.
31. (b) Toone, E. J.; Jones, J. B. Tetrahedron: Asymmetry 1991, 2, 1041-1052.
32. (c) Cornforth, J. W.; Cornforth, R. H.; Popjak, G.; Yengoyan, L. J. Biol. Chem. 1966, 241, 3970-3987.