Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 9
177
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Preparation of γ-Hydroxynitriles via Nitrile Enolate-Epoxide Reactions: Scope and Diastereoselectivity

, , , , &
Pages 1691-1701 | Received 02 Nov 1997, Published online: 22 Aug 2006

REFERENCES

  • Rappoport , Z. ed. 1970 . The Chemistry of the Cyano Group , New York : Interscience .
  • Arseniyadis , S. , Kyler , K. S. and Watt , D. S. 1984 . Organic Reactions , Edited by: Dauben , W. G. Vol. 31 , New York : Wiley . Chapter 1.
  • For representative examples see: (a) Pirkle W. H. Adams P. E. J. Org. Chem. 1979 44 2169
  • Gopalan , A. , Lucero , R. , Jacobs , H. and Berryman , K. 1991 . Synth. Commun. , 21 : 1321
  • Matsuda , I. , Murata , S. and Ishii , Y. 1979 . J. Chem. Soc., Perkin Trans. 1 , : 26
  • Katagiri , T. , Akizuki , M. , Kuriyama , T. , Shinke , S. and Uneyama , K. 1997 . Chem. Lett. , : 549
  • Taylor , S. K. , Chmiel , N. H. , Simons , L. J. and Vyvyan , J. R. 1996 . J. Org. Chem. , 61 : 9084
  • Stork , G. , Cama , L. D. and Coulson , D. R. 1974 . J. Am. Chem. Soc. , 96 : 5268
  • Stork , G. and Cohen , J. F. 1974 . J. Am. Chem. Soc. , 96 : 5270
  • Murata , S. and Matsuda , I. 1978 . Synthesis , : 221
  • Matsuda , I. , Murata , S. and Izumi , Y. 1979 . Bull. Chem. Soc. Jpn. , 52 : 2389
  • Matsuda , I. , Murata , S. and Izumi , Y. 1980 . J. Org. Chem. , 45 : 237
  • Larchevêque , M. and Debal , A. 1980 . Synth. Commun. , 10 : 49 and references therein.
  • Taylor , S. K. , Fried , J. K. , Grassl , Y. N. , Marolewski , A. E. , Pelton , E. A. , Poel , T.-J. , Rezenka , D. S. and Whittaker , M. R. 1993 . J. Org. Chem. , 58 : 7304 and references therein
  • Sturm , T.-J. , Marolewski , A. E. , Rezenka , D. S. and Taylor , S. K. 1989 . J. Org. Chem. , 54 : 2039 and references therein
  • This was determined by converting 5c to the corresponding lactone via microbial nitrile hydrolysis3 (known not to epimerize α-stereocenters) and comparing the 1H NMR resonances for the major isomer to literature data of known cis and trans 2,4-disubstituted lactones.
  • Carlier , P. R. , Lo , K. M. , Lo , M. M.-C. and Williams , I. D. 1995 . J. Org. Chem. , 60 : 7511

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.