Practical methodology for the asymmetric synthesis of organofluorine compounds

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1335-1338

  Myers, Andrew G ^a   McKinstry, Lydia ^a   Barbay, Joseph K ^a   Gleason, James L ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; FLUORINE DERIVATIVE; HALIDE; ORGANOFLUORINE DERIVATIVE;

ALKYLATION; ARTICLE; CRYSTAL; DIASTEREOISOMER; ENANTIOMER; METHODOLOGY; SOLID; SYNTHESIS;

EID: 0032510349     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00152-X     Document Type: Article

References (14)

1. 1. (a) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Studies in Organic Chemistry 48; Elsevier: New York, 1993.
2. (b) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, 1996.
3. 2. Reviews: (a) Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111.
4. (b) Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661.
5. Recent and noteworthy asymmetric C-C(F) bond forming methodology: (c) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem . 1993, 58, 2454.
6. (d) Less, S. L.; Handa, S.; Millburn, K.; Leadlay, P. F.; Dutton, C. J.; Staunton, J. Tetrahedron Lett. 1996, 37, 3515.
7. 3. (a) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
8. (b) Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555.
9. (c) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488.
10. (d) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
11. (e) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, in press.
12. 4. Kurth, M. J.; Green, C. B.; Mount, M. E.; Jackson, D. Y. Int. J. Peptide Protein Res. 1988, 31, 388.
13. 5. The use of trifluoroethanol as solvent is critical to avoid cyclization of the product by internal displacement of fluoride with the hydroxyl group of the auxiliary, a side reaction that occurs when other solvents are used.
14. 6. For earlier studies of the stereochemistry of fluoroacetate-derìved enolates, see: Welch, J. T.; Plummer, J. S.; Chou, T.-S. J. Org. Chem. 1991, 56, 353.