Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 12
50
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Synthesis of the Cyanofluoromethylated Ketones: Michael Reaction of the Cyanofluoromethyl Anion Species to Unsaturated Ketones

, , , &
Pages 2277-2287 | Received 15 Dec 2003, Published online: 17 Aug 2006

References

  • Banks , R. E. 1979 . Organofluorine Chemicals and Their Industrial Applications London : Soc. Chem. Ind. .
  • Filler , R. and Kobayashi , Y. 1982 . Biomedical Aspects of Fluorine Chemistry Tokyo : Kodansha Ltd .
  • Liebman , J. K. , Greenberg , A. and Dolbier , W. R. Jr. 1988 . Fluorine‐Containing Molecules, Structure, Reactivity, Synthesis New York : VCH .
  • Takeuchi , Y. 1988 . Building blocks for the preparation of monofluoro organic compounds . J. Syn. Org. Chem. Jpn , 46 ( 2 ) : 145 – 159 .
  • Welch , J. T. and Eshwarakrishman , S. 1991 . Fluorine in Bioorganic Chemistry New York : Wiley .
  • Takeuchi , Y. , Takagi , K. , Yamada , T. , Nabetani , M. and Koizumi , T. 1994 . Synthetic studies for novel structure of α‐nitrogenously functionalized α‐fluorocarboxylic acids. Part III. Some reactions of α‐bromo‐α‐fluorocarboxylic acids and their ethyl esters with sodium azide . J. Fluorine Chem. , 68 ( 2 ) : 149 – 154 . [CROSSREF]
  • Takeuchi , Y. , Kawahara , S. , Suzuki , S. and Koizumi , T. 1996 . First electronic investigation of the structure of alkenes compatible to carbon radicals bearing a single fluorine atom . J. Org. Chem. , 61 ( 1 ) : 301 – 303 . [CROSSREF]
  • Takeuchi , Y. 1997 . Synthesis and reactivity of multifunctional carbon compounds . J. Syn. Org. Chem. Jpn , 55 ( 10 ) : 886 – 896 .
  • Yokoyama , Y. , Suzuki , S. , Furihata , H. , Takahi , S. , Nomura , M. and Kajitani , M. 2004 . The development of a novel synthetic method of cyanofluoroamides using the cobaltadithiolene complex . Synthesis , : 701 – 705 .
  • Yokoyama , Y. and Mochida , K. 1998 . Germyl anion species‐promoted formation of cyanofluoromethylene compounds: first and efficient synthesis of fluorinated homoallylic and homo‐2‐propynylic cyanides . Chem. Commun. , : 1093 – 1094 . [CROSSREF]
  • Yokoyama , Y. and Mochida , K. 1999 . Chemoselective syntheses of various cyanofluoromethylene compounds from organic bromides by use of sodium triethylgermanate(IV) and its mechanistic studies . Synthesis , : 676 – 682 . [CROSSREF]
  • Welch , J. T. and Eswarakrishnan , S. 1985 . Improved procedure for introducing the α‐fluoroacetyl group via the directed aldol reaction . J. Org. Chem. , 50 ( 25 ) : 5403 – 5405 .
  • Welch , J. T. and Eswarakrishnan , S. 1985 . A short synthesis of 2‐deoxy‐2‐fluoro‐ribo‐D‐pentopyranose . J. Chem. Soc. Chem. Commun. , : 186 – 188 . [CROSSREF]
  • Kitazume , T. and Ikeya , T. 1988 . A microbially based aldol reaction for the preparation of fluorinated carbinols . Chem. Express , 3 ( 10 ) : 611 – 614 .
  • Welch , J. T. and Herbert , R. W. 1990 . The stereoselective construction of (Z)‐3‐aryl‐2‐fluoroalkenoates . J. Org. Chem. , 55 ( 16 ) : 4782 – 4784 .
  • Araki , K. , Wichtowski , J. A. and Welch , J. T. 1991 . The stereoselective synthesis of 3‐fluoro‐azetidinones . Tetrahedron Lett. , 32 ( 40 ) : 5461 – 5464 . [CROSSREF]
  • Ishihara , T. , Ichihara , K. and Yamanaka , H. 1995 . Highly stereoselective aldol reaction of metal enolates of α‐fluoropropanethioates with aldehydes affording erythro‐α‐fluoro‐α‐methyl‐β‐hydroxy alkanethioates . Tetrahedron Lett. , 36 ( 45 ) : 8267 – 8270 .
  • Ishihara , T. , Ichihara , K. and Yamanaka , H. 1996 . Stereoselective synthesis of 3‐fluoro azetidinones via the condensation of 2‐fluoropropanethioate lithium enolate with imines . Tetrahedron , 52 ( 1 ) : 255 – 262 . [CROSSREF]
  • Yokoyama , Y. and Mochida , K. 1998 . Stereoselective syntheses of 2‐fluoro‐2‐methyl‐3‐hydroxypropionamides by use of a germyl anion species . Synlett , : 37 – 38 . and references cited there in
  • Pews , R. G. and Lysenko , Z. 1985 . Synthesis of halogenated pyridines via the copper(I) chloride‐catalyzed addition of polyhaloacetonitriles to olefins . J. Org. Chem. , 50 ( 25 ) : 5115 – 5119 .
  • Bulten , E. J. and Noltes , J. G. 1966 . Organogermaniurn compounds. VI. Trialkylgermanyl alkali metal derivatives . Tetrahedron Lett. , : 4389 – 4392 . [CROSSREF]
  • Bulten , E. J. and Noltes , J. G. 1967 . Reactivity of trialkylgermyl alkali metal derivatives . Tetrahedron Lett. , : 1443 – 1447 . [CROSSREF] [CSA]

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.