Novel reaction of allylic alcohols with a hexafluoropropene-diethylamine adduct (PPDA) to form α-fluoro-α-(trifluoromethyl)-γ,δ-unsaturated amides

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 305-308

  Ogu, Ken Ichi ^a   Akazome, Motohiro ^a   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; AMIDE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032518887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10548-2     Document Type: Article

References (25)

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19. 2O: C, 55.88; H, 7.84; N, 4.66. Found: C, 55.92; H,7.91; N, 4.59.
20. 10. When the reaction time was shortened to 1 h, we obtained cinnamy 12,3,3,3-tetrafluoropropionate (i) in 25% yield along with 4a (14%). After more than 25 h, the ester (i) was not observed in the reaction mixture. These facts suggest that the compound (6) in Scheme 1 is a common intermediate of 4a and the ester (i), which is formed by hydrolysis (aqueous workup) of 6, and that elongation of the reaction time completes the [3,3]sigmatropic rearrangement of 6 to produce 4a.
21. 3, Z =2, R = 0.066, Rw = 0.070, T=173 K. One ethyl group of 4a was disordered.
22. 12. Recently, iodolactonization of a fluorinated compound has been reported: Konno, T.; Kitazume, T. Tetrahedron Asymmetry, 1997, 8, 223.
23. 13. The p-toly lsulfony 1 derivative was obtained by the substitution of 7c with sodium p-toluenethiolate in DMSO followed by the oxidation with MCPBA (2 equiv).
24. 14. Crystal data of 9 : monoclinic, space group P21/a = 9.823(3) Å, b = 27.343(7) Å, c = 5.755(2) Å, β = 103.81(2)°, V= 1501.1(7) Å3, Z = 4, R = 0.076, Rw = 0.091, T=173 K.
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