Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates

Synlett

Volumn , Issue 5, 2004, Pages 791-794

  Andrews, Philip C ^a   Bhaskar, Vijaya ^a,c   Bromfield, Karen M ^a   Dodd, Aileen M ^a   Duggan, Peter J ^a   Duggan, Sandhya A M ^a,d   McCarthy, Tom D ^b,e  

^a MONASH UNIVERSITY   (Australia)

^b Biomolecular Research Institute   (Australia)

^c Kinacia Pty Ltd   (Australia)

^d Mayne Pharma Pty Ltd   (Australia)

^e Starpharma Holdings Limited   (Australia)

Author keywords

Conjugate additions; Diastereoselectivity; Fluorination; Lithium amides; amino acids

Indexed keywords

CINNAMIC ACID DERIVATIVE; ESTER DERIVATIVE; FLUOROBENZENE; LITHIUM; METHYL GROUP; PHENYLALANINE; SULFONAMIDE;

ADDITION REACTION; ANALYTIC METHOD; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; ENANTIOMER; FLUORINATION; STEREOCHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 1942457208     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817782     Document Type: Article

References (26)

1. (a) Welch, J. T. Tetrahedron 1987, 43, 3123.
2. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
3. (c) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, 1996.
4. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley: Chichester UK, 1999.
5. Frey, P. A.; Magnusson, O. T. Chem. Rev. 2003, 103, 2129.
6. Walker, B.; Lynas, J. F. Cell Mol. Life Sci. 2001, 58, 596.
7. Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yasuda, N.; Uekusa, H.; Ono, T.; Berbasov, D. O.; Soloshonok, V. A. J. Org. Chem. 2003, 68, 7448.
8. Somekh, L.; Shanzer, A. J. Am. Chem. Soc. 1982, 104, 5836.
9. Charvillon, F. B.; Amouroux, R. Tetrahedron Lett. 1996, 37, 5103.
10. For solid state structures of 2 and related amides, see: (a) Andrews, P. C.; Duggan, P. J.; Fallon, G. D.; McCarthy, T. D.; Peatt, A. C. J. Chem. Soc., Dalton Trans. 2000, 1937. (b) Andrews, P. C.; Duggan, P. J.; Fallon, G. D.; McCarthy, T. D.; Peatt, A. C. J. Chem. Soc., Dalton Trans. 2000, 2505. (c) Andrews, P. C.; Duggan, P. J.; Maguire, M.; Nichols, P. J. J. Chem. Soc., Chem. Commun. 2001, 53.
11. For solid state structures of 2 and related amides, see: (a) Andrews, P. C.; Duggan, P. J.; Fallon, G. D.; McCarthy, T. D.; Peatt, A. C. J. Chem. Soc., Dalton Trans. 2000, 1937. (b) Andrews, P. C.; Duggan, P. J.; Fallon, G. D.; McCarthy, T. D.; Peatt, A. C. J. Chem. Soc., Dalton Trans. 2000, 2505. (c) Andrews, P. C.; Duggan, P. J.; Maguire, M.; Nichols, P. J. J. Chem. Soc., Chem. Commun. 2001, 53.
12. For solid state structures of 2 and related amides, see: (a) Andrews, P. C.; Duggan, P. J.; Fallon, G. D.; McCarthy, T. D.; Peatt, A. C. J. Chem. Soc., Dalton Trans. 2000, 1937. (b) Andrews, P. C.; Duggan, P. J.; Fallon, G. D.; McCarthy, T. D.; Peatt, A. C. J. Chem. Soc., Dalton Trans. 2000, 2505. (c) Andrews, P. C.; Duggan, P. J.; Maguire, M.; Nichols, P. J. J. Chem. Soc., Chem. Commun. 2001, 53.
13. (a) Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183.
14. (b) Davies, S. G.; Garrido, N. M.; Ichihara, O.; Walters, I. A. S. J. Chem. Soc., Chem. Commun. 1993, 1153.
15. (a) Bunnage, M. E.; Chernega, A. N.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2373.
16. (b) Brackenridge, I.; Davies, S. G.; Fenwick, D. R.; Ichihara, O.; Polywka, M. E. C. Tetrahedron 1999, 55, 533.
17. Davies, S. G.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129.
18. (a) Davies, S. G.; Fenwick, D. R. Chem. Commun. 1997, 565.
19. (b) Davies, S. G.; Smethurst, C. A. P.; Smith, A. D.; Smyth, G. D. Tetrahedron: Asymmetry 2000, 11, 2437.
20. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737.
21. 3): δ = -187.7 (dd, J = 20 and 50 Hz).
22. 3): δ = -201.1 (dd, J = 28 and 49 Hz).
23. Davies, S. G.; Ichihara, O.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1141.
24. 2. All H atoms were placed in calculated positions (C-H 0.95 Å) and included in the final least-squares refinement. All other atoms were located and refined anisotropically. Flack parameters were indeterminate since no heavy atoms are present and absolute stereochemistry was based on the stereochemistry of the starting amine (see text). Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 175705 for 4a and 175706 for 4b. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail:]
25. (b) Sheldrick, G. M. SHELXS 97, Program for the Solution of Crystal Structures; University of Göttingen: Germany, 1997.
26. 3OH).