Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 18
508
Views
23
CrossRef citations to date
0
Altmetric
Original Articles

KF/Al2O3-Mediated Michael Addition of Thiols to Electron‐Deficient Olefins

, &
Pages 2427-2433 | Received 11 Jan 2005, Published online: 18 Aug 2006

References

  • Bull , S. D. , Davies , S. G. , Delgado‐Ballester , S. , Fenton , G. , Kelly , P. M. and Smith , A. D. 2000 . The asymmetric synthesis of beta‐haloaryl‐beta‐amino acid derivatives . Synlett , 9 : 1257 – 1260 .
  • Rosenthal , D. , Braundrup , G. , Davis , K. H. and Wall , M. E. 1965 . The synthesis of beta‐amino mercaptans and beta‐amino thiosulfates via ethylenimine intermediates . J. Org. Chem. , 30 ( 11 ) : 3689 – 3696 .
  • Ranu , B. C. and Dey , S. S. 2004 . Catalysis by ionic liquid: A simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br . Tetrahedron , 60 ( 19 ) : 4183 – 4188 .
  • Ranu , B. C. , Dey , S. S. and Hajra , A. 2003 . Catalysis by an ionic liquid: Efficient conjugate addition of thiols to electron‐deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent‐free conditions . Tetrahedron , 59 ( 14 ) : 2417 – 2421 .
  • Alam , M. M. , Varala , R. and Adapa , S. R. 2003 . Conjugate addition of indoles and thiols with electron‐deficient olefins catalyzed by Bi(OTf)3 . Tetrahedron Lett. , 44 ( 27 ) : 5115 – 5119 .
  • Yadav , J. S. , Reddy , B. V. S. and Gakul , B. 2003 . Green protocol for conjugate addition of thiols to α,β‐unsaturated ketons using a [Bmim]PF6/H2O system . J. Org. Chem. , 68 ( 18 ) : 7098 – 7100 .
  • Benjamin , E. B. 2002 . KF/Al2O3‐mediated organic synthesis . Tetrahedron , 58 ( 46 ) : 9301 – 9320 .
  • Schmittling , E. A. and Sawyer , S. S. 1991 . Selective desilylation of tert‐butyldimethylsilyl ethers of phenols using potassium fluoride‐alumina and ultrasound . Tetrahedron Lett. , 32 ( 49 ) : 7207 – 7210 .
  • Dike , S. Y. , Ner , D. H. and Kumar , A. 1991 . A new chemoenzymatic enantioselective synthesis of optically active benzothiopyran and benzothiazepin ring system . Synlett , : 443 – 444 .
  • Eliel , E. L. and Knox , D. E. 1985 . Neighbouring group participation by sulfur involving four‐membered ring intermediates (RS‐4) . J. Am. Chem. Soc. , 107 ( 10 ) : 2946 – 2952 .
  • Beckwith , A. L. J. and Easton , C. J. 1983 . Formation of β‐lactams from 3‐phenylthiopropionamide derivatives: A possible model for penicillin biosynthesis . Tetrahedron , 39 ( 23 ) : 3995 – 4001 .
  • Baldwin , J. E. and Davis , A. P. 1981 . Penicilin biosynthesis: A model for the oxidative cyclisation of a peptide to a β‐lactam . J. Chem. Soc., Chem. Commun. , : 1219 – 1221 .
  • Kaneko , T. 1985 . Possible biomimetic synthesis of beta‐lactams . J. Am. Chem. Soc. , 107 ( 19 ) : 5490 – 5492 .
  • Krishnan , G. and Sampson , P. 1990 . Synthesis of β‐fluoro‐α,β‐unsaturated esters and nitriles via a fluoro‐pummerer rearrangement . Tetrahedron Lett. , 31 ( 39 ) : 5609 – 5612 .

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.