Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine

Tetrahedron Letters

Volumn 51, Issue 4, 2010, Pages 683-685

  Kim, Joong Gon ^a   Jang, Doo Ok ^b  

^a Hanwha Corporation   (South Korea)

^b Yonsei University Wonju   (South Korea)

Author keywords

Amine; Aminoalcohol; Trichloroacetonitrile; Trifluoroacetic acid; Trifluoroacetlyation; Triphenylphosphine

Indexed keywords

ACETONITRILE DERIVATIVE; AMINE; TRIFLUOROACETIC ACID; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; RACEMIZATION;

EID: 72149127886     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.105     Document Type: Article

References (22)

1. Green T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 4th ed. (2007), Wiley-Interscience, New York
2. Friestad G.K., and Banerjee K. Org. Lett. 11 (2009) 1095
3. Schallenberg E.E., and Calvin M. J. Am. Chem. Soc. 77 (1955) 2779
4. Forbus Jr. T.R., Taylor J.C., and Martin J.C. J. Org. Chem. 52 (1987) 4156
5. Bergeron R.J., and McMains J.S. J. Org. Chem. 53 (1988) 3108
6. Katritzky A.R., Yang B., Qiu G., and Zhang Z. Synthesis (1999) 55
7. Staab H.A., and Walter G. Angew. Chem. 72 (1960) 35
8. Katritzky A.R., Yang B., and Semenzin D. J. Org. Chem. 62 (1997) 726
9. Keumi T., Shimada M., Morita T., and Kitajima H. Bull. Chem. Soc. Jpn. 63 (1990) 252
10. Katja Heinze K., and Hempel K. Chem. Eur. J. 15 (2009) 1346
11. Beyermann M., Bienert M., Niedrich H., Carpino L.A., and Sadat-Aalaee D. J. Org. Chem. 55 (1990) 721
12. Yu S.K.T., and Green J.B. Anal. Chem. 61 (1989) 1260
13. Fieser L.F., and Fieser M. Reagents for Organic Synthesis (1967), John Wiley & Sons, New York p 1221
14. Narang A.S., and Vince R. J. Med. Chem. 20 (1977) 1684
15. Salazar J., López S.E., and Rebollo O. J. Fluorine Chem. 124 (2003) 111
16. Ohtaka J.O., Sakamoto T., and Kikugawa Y. Tetrahedron Lett. 50 (2009) 1681
17. López S.E., Pérez Y., Restrepo J., Salazar J., and Charris J. J. Fluorine Chem. 128 (2007) 566
18. Jang D.O., Park D.J., and Kim J. Tetrahedron Lett. 40 (1999) 5323
19. Jang D.O., Cho D.H., and Kim J.-G. Synth. Commun. 33 (2003) 2885
20. 3).
21. 6) δ 56.1, 63.5, 115.8, 126.7, 127.3, 127.9, 138.9, 156.2.
22. Chiral HPLC analysis for (R)-2,2,2-trifluoro-N-(2-hydroxy-1-phenylethyl)acetamide: Diacel Chiralcel OC; n-hexane/IPA (70/30 v/v); flow rate = 1.0 mL/min; UV (λ = 254 nm); retention time for R form = 15.2 min; retention time for S form = 23.5 min.