Synthesis of 1-fluoroindan-1-carboxylic acid (FICA) and its properties as a chiral derivatizing agent

Journal of Fluorine Chemistry

Volumn 127, Issue 6, 2006, Pages 760-768

  Takahashi, Tamiko ^a,b   Kameda, Hiroaki ^b   Kamei, Tomoyo ^a   Ishizaki, Miyuki ^a  

^a JOSAI INTERNATIONAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

F; H; 1 Fluoroindan 1 carboxylic acid; Chiral derivatizing agent

Indexed keywords

EID: 33646506838     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.02.008     Document Type: Article

References (18)

1. Kusumi T. Synth. Org. Chem. Jpn. 51 (1993) 462-470
2. Takeuchi Y., and Takahashi T. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-organic Compounds (1999), Wiley, Chichester (Chapter 16)
3. Seco J.M., Quinoa E., and Riguera R. Chem. Rev. 104 (2004) 17-117
4. Kasai Y., Naito J., Kuwahara S., Watanabe M., Ichikawa A., and Harada N. Synth. Org. Chem. Jpn. 62 (2004) 1114-1127
5. Kusumi T., Yabuuchi T., Takahashi H., and Ooi T. Synth. Org. Chem. Jpn. 63 (2005) 1102-1114
6. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092-4096
7. Latypov Sh.K., Seco J.M., Quinoa E., and Riguera R. J. Org. Chem. 61 (1996) 8569-8577
8. Takahashi T., Fukushima A., Tanaka Y., Takeuchi Y., Kabuto K., and Kabuto C. Chem. Commun. (2000) 788-789
9. One rotamer designated sp has the C-F and C{double bond, long}O bonds in a synperiplanar arrangement and the other denoted ap contains these bonds in an antiperiplanar arrangement.
10. Vedejs E., Engler D.A., and Telschow J.E. J. Org. Chem. 43 (1978) 188-195
11. Middleton W.J. J. Org. Chem. 40 (1975) 574-578
12. Org. Synth. Collect 8 (1993) 350-353.
13. The esters of R-acids with R-alcohols are designated RR, and those of S-acids with R-alcohols are denoted SR.
14. Each stereocenter of FICA part of 5ia and 5ib was tentatively assigned as R and S on the assumption that the sp rotamer is more stable than the ap one. See Refs. [2-4].
15. 3 groups are arranged similarly on the stereocenters, the absolute configurations of FICA and MTPA is opposite because of priority of the substituents.
16. Noland W.E., Landucci L.L., and Kameswaran V. J. Org. Chem. 45 (1980) 3456-3461
17. Katz C.E., and Aube J. J. Am. Chem. Soc. 125 (2003) 13948-13949
18. Friedrich E.C., and Taggart D.B. J. Org. Chem. 40 (1975) 720-723