Efficient parallel resolution of an active ester of 2-phenylpropionic acid using quasi-enantiomeric Evans' oxazolidinones

Tetrahedron Letters

Volumn 46, Issue 16, 2005, Pages 2897-2902

  Coumbarides, Gregory S ^a   Dingjan, Marco ^a   Eames, Jason ^a   Flinn, Anthony ^b   Northen, Julian ^b   Yohannes, Yonas ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^b Onyx Scientific Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; HYDRATROPIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PENTAFLUOROPHENYL 2 PHENYLPROPIONIC ACID; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; DIASTEREOISOMER; ENANTIOMER; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 15944408858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.139     Document Type: Article

References (36)

1. R. Noyori, K. Nagai, and M.J. Kitamura J. Org. Chem. 52 1987 3176
2. J.K. Stille, and G.J. Parinello J. Mol. Catal. 21 1983 203
3. H. Alper, and H. Nathalie J. Am. Chem. Soc. 112 1990 2803
4. T. Hiyami, and N. Wasake Tetrahedron Lett. 26 1985 3259
5. R.D. Larson, E.G. Corely, P. Davis, P.J. Reider, and E.J.J. Grabowski J. Am. Chem. Soc. 111 1989 7650
6. A. Kumar, R.V. Salunke, R.A. Rane, and S.Y. Dike J. Chem. Soc., Chem. Commun. 1991 485
7. D.A. Evans, M.D. Ennis, and D.J. Mathrp J. Am. Chem. Soc. 104 1982 1737
8. D.A. Evans Aldrichim. Acta 15 1982 23
9. Yohannes, Y. Ph.D. Thesis, University of London, 2004
10. G.S. Coumbarides, J. Eames, A. Flinn, J. Northen, and Y. Yohannes Tetrahedron Lett. 46 2005 849
11. For a comprehensive study into the conformational effects of oxazolidinones see: S.D. Bull, S.G. Davies, M.-S. Key, R.L. Nicholson, and E.D. Savory Chem. Commun. 2000 1721 It appears this diastereoselectivity is lowered to 92:8 (anti-2: syn-2) by quenching the resulting lithium enolate with MeI at 0°C
12. S.G. Davies, and H. Sanganee Tetrahedron: Asymmetry 6 1995 671
13. S.D. Bull, S.G. Davies, S. Jones, M.E.C. Polywka, R.S. Prasad, and H. Sanganee Synlett 1988 519
14. S.D. Bull, S.G. Davies, S. Jones, and H. Sanganee J. Chem. Soc., Perkin. Trans. 1 1999 387
15. D. Seebach, and T. Hintermann Helv. Chim. Acta 81 1998 2093
16. For a related kinetic resolution see: S.-I. Fukuzawa, Y. Chion, and T. Yokoyama Tetrahedron: Asymmetry 13 2002 1645
17. S.P. Bew, S.G. Davies, and S.-I. Fukuzawa Chirality 12 2000 483
18. For recent reviews see: J. Eames Angew. Chem., Int. Ed 39 2000 885
19. J. Eames Parallel Kinetic Resolutions Organic Synthesis Highlights Vol. V 2003 VCH-Wiley Weinheim 3-527-30611-0 151 Chapter 17
20. J.R. Dehli, and V. Gotor Chem. Soc. Rev. 31 2002 365
21. L. Liao, F. Zhang, O. Dmitrenko, R.D. Bach, and J.M. Fox J. Am. Chem. Soc. 126 2004 4490
22. M. Adamczyk, J.R. Fishpaugh, and K.J. Heuser Bioconjugate Chem. 8 1987 253
23. J.M. Salvino, N.V. Kumar, E. Orton, J. Airey, T. Kiesow, K. Crawford, R. Mathew, P. Krolikowski, M. Drew, D. Engers, D. Krolikowski, T. Herpin, M. Gardyan, G. McGeehan, and R. Labaudiniere J. Comb. Chem. 2 2000 691
24. L. Kisfaludy, J.E. Roberts, R.H. Johnson, G.L. Mayers, and J. Kovacs J. Org. Chem. 35 1970 3563
25. J. Kovacs, R.E. Cover, R.H. Johnson, T.J. Kallas, G.L. Mayers, and J.E. Roberts J. Org. Chem. 38 1973 2518
26. X-ray crystallography has revealed the pentafluorophenyl ring to be near-orthogonal to the carbonyl group. For representative examples see: M. Czugler, G. Argay, M. Low, and L. Kisfaludy Hung. Diff. Conf. 8 1978 7
27. B. Chan, E.W. Tan, and A.G. Blackman Acta Crystallogr., Sect. E. Struct. Rep. Online 57 2001 725
28. E. Mann, J. Mahia, M.A. Maestro, and B. Herradon J. Mol. Struct. 641 2002 101
29. E.W. Tan, B. Chan, and A.G. Blackman J. Am. Chem. Soc. 124 2002 2078
30. S. Boisnard, A.-C. Carbonnelle, and J. Zhu Org. Lett. 3 2001 2061
31. R.W. Scott, J. Epperson, and C.H. Heathcock J. Org. Chem. 63 1998 5001
32. E.A. Wintner, M.M. Conn, and J. Rebek J. Am. Chem. Soc. 116 1994 8877
33. W. Kurosawa, T. Kan, and T. Fukuyama J. Am. Chem. Soc. 125 2003 8112
34. M. Prashad, D. Har, H.-Y. Kim, and O. Repic Tetrahedron Lett. 39 1998 7067
35. N. Kise, K. Kumada, Y. Terao, and N. Ueda Tetrahedron 54 1998 2697 For additional discussion of these derivatives see Refs. 5 and 8
36. Crystallographic data has been deposited with the Cambridge Crystallographic Data Centre (reference numbers 259956 and 259957)