Enantioselective synthesis of 2-fluoro carboxylic acids from trichloromethyl carbinols: An efficient approach to chiral fluorine introduction into insect sex pheromones

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 37-40

  Khrimian, Achot P ^a,b   Oliver, James E ^c   Waters, Rolland M ^c   Panicker, Sini ^a   Nicholson, Jesse M ^a   Klun, Jerome A ^c  

^a HOWARD UNIVERSITY   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

^c AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ORGANOFLUORINE DERIVATIVE; PHEROMONE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030048684     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00415-7     Document Type: Article

References (21)

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3. Klun, J. A.; Oliver, J. E. 207th ACS National Meeting, San Diego, 1994; Book of Abstracts, part 1, Division of Agrochemicals, paper 120.
4. (a) Lowe, G.; Potter, B. V. L.; J. Chem. Soc., Perkin Trans. I 1980, 2029-2032.
5. (b) Faustini, F.; De Munari, S.; Panzeri, A.; Villa, V.; Gandolfi, C. A. Tetrahedron Lett. 1981, 22, 4533-4536.
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10. 1H NMR: 0.95 (t, 3H), 1.41 (m, 3H), 1.63 (m, 2H), 2.06 (m, 1H), 4.01 (dd, 1H, J = 9.6 and 2.0 Hz, CHOH).
11. 2C=O).
12. 3);
13. 3COOH, afforded fluoroacids 3 and chloroacids 4 (Table 1). A small amount (3-5%) of a byproduct, which we believe to be the corresponding 2-hydroxyacid, was also found in the acidic extract.
14. 2 for 3-4 h. After evaporation in vacuo, the residue was treated with (S)-α methylbenzylamine (3 μL) in benzene for 3 h, and the resulting amides were analyzed by GC on a SPB-1 capillary column (60 m × 0.25 mm, film 0.25 μm, Suppelco).
15. Kalaritis, P.; Regenye, R. W.; Partridge, J. J.; Coffen, D. L. J. Org. Chem. 1990, 55, 812-815.
16. Elimination of hydrogen chloride from the alcohol 1 provided external source of chloride which can compete with fluoride in the epoxide ring opening.
17. Reeve, W.; McKee, J. R.; Brown, R.; Lakshmanan, S.; McKee, G. A. Can. J. Chem. 1980, 55, 485-493.
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19. Landini, D.; Maia, A.; Rampoldi, A. J. Org. Chem. 1989, 54, 328. Cox, D. P.; Terpinski, J.; Lawrynowicz, W. J. Org. Chem. 1984, 549, 3216.
20. Mosher esters were prepared from (+)-MTPA according to Sreinz, L.; Valterova, I.; Wimmer, Z.; Budesinsky, M.; Saman, D.; Kohoutova, J.; Romanuk, M.; Vrkoc, J. Collect. Czech. Chem. Commun. 1986, 51, 2207, and analyzed by GC on a SPB-1 column.
21. 3): - 187.7.