Asymmetric aldol reactions using a fluorous oxazolidinone chiral auxiliary

Synlett

Volumn , Issue 5, 2003, Pages 635-638

  Hein, Jason E ^a   Hultin, Philip G ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Aldol reactions; Asymmetric synthesis; Chiral auxiliaries; Fluorous extraction; Fluorous supported synthesis

Indexed keywords

OXAZOLIDINONE DERIVATIVE; PHENYLALANINE; SILICON DIOXIDE; TITANIUM;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE EXTRACTION; STANDARD; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037267172     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38371     Document Type: Article

References (29)

1. Watson, C. Angew. Chem. Int. Ed. 1999, 38, 1903.
2. (a) Reggelin, M.; Brenig, V.; Zur, C. Org. Lett. 2000, 2, 531.
3. (b) Paterson, I.; Donghi, M.; Gerlach, K. Angew. Chem. Int. Ed. 2000, 39, 3315.
4. (a) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777.
5. (b) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655.
6. (c) Burgess, K.; Lim, D. Chem. Commun. 1997, 785.
7. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
8. Lopez-Pelegrin, J. A.; Janda, K. D. Chem.-Eur. J. 2000, 6, 1917.
9. Hultin, P.G. unpublished results.
10. Sudharshan, M. M.Sc. Thesis; University: Manitoba, 1999.
11. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
12. Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714.
13. Luo, Z.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766.
14. (a) Zhang, W.; Luo, Z.; Chen, C. H.-T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443.
15. (b) Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855.
16. (c) Nakamura, Y.; Takeuchi, S.; Okumura, K.; Ohgo, Y.; Curran, D. P. Tetrahedron 2002, 58, 3963.
17. Lewis, N.; McKillop, A.; Taylor, R. J. K.; Watson, R. J. Synth. Commun. 1995, 25, 561.
18. (a) Gassman, P. G.; O'Reilly, N. J. Tetrahedron Lett. 1985, 26, 5243.
19. (b) Uno, H.; Shiraishi, Y.; Suzuki, H. Bull. Chem. Soc. Jpn. 1989, 62, 2636.
20. 3: C, 37.58; H, 2.21; N, 2.19. Found: C, 37.42; H, 2.01; N, 2.04.
21. Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045.
22. Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1987, 28, 6331.
23. Luo, Z.; Williams, J.; Read, R. W.; Curran, D. P. J. Org. Chem. 2001, 66, 4261.
24. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaundhary, K. J. Org. Chem. 2001, 66, 894.
25. 2O removed all inorganic and organic impurities. Fluorous material was then isolated by eluting with ca. 20 mL of acetone to give 0.11 g (95%) of the product 11, which was analyzed by HPLC.
26. Billiet, H. A. H.; Schoenmakers, P. J.; De Galan, L. J. Chromatogr. 1981, 218, 443.
27. Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489.
28. Evans, D. A.; Britton, T.; Ellman, J. A. Tetrahedron Lett. 1987, 49, 6141.
29. Wu, Y.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428.