Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 19
2,697
Views
36
CrossRef citations to date
0
Altmetric
Original Articles

Aza-Michael Addition of Amines to α,β-Unsaturated Compounds Using Molecular Iodine as Catalyst

, &
Pages 2830-2836 | Received 06 May 2009, Published online: 25 Aug 2010

REFERENCES

  • (a) Lee , V. J. In Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon Press : New York , 1991 ; vol. 4 , chap. 1.2.69; (b) Cardillo , G. ; Tomasini , C. Asymmetric synthesis of β-amino acids and α-substituted β-amino acids. Chem. Soc. Rev. 1996, 25, 117–128; (c) Muller , T. E. ; Beller , M. Metal-initiated amination of alkenes and alkynes. Chem. Rev. 1998, 98, 675–704; (d) Hong , S. ; Marks , T. J. Organolanthanide-catalyzed hydroamination. Acc. Chem. Res. 2004, 37, 673–686.
  • (a) Devine , P. N. ; Heid , R. M. ; Tschaen , D. M. Stereoselective synthesis of 2-aryloxy esters: An asymmetric approach to fluoxetine, tomoxetine, and nisoxetine . Tetrahedron 1997 , 53 , 6739 – 6746 ; (b) Xu , L.-W. ; Xia , C.-G. A catalytic enantioselective aza-Michael reaction: Novel protocols for asymmetric synthesis of β-amino carbonyl compounds . Eur. J. Org. Chem. 2005 , 633 – 639 ; (c) Traxler , P. ; Trinks , U. ; Buchduger , E. ; Mett , H. ; Meyer , T. ; Muller , M. ; Regenass , U. ; Rosel , J. ; Lydon , N. [(Alkylamino)methyl]acrylophenones: Potent and selective inhibitors of the epidermal growth factor receptor protein tyrosine kinase . J. Med. Chem. 1995 , 38 , 2441 – 2448 .
  • (a) Bull , S. D. ; Davies , S. G. ; Delgado-Ballester , S. ; Fenton , G. ; Kelly , P. M. ; Smith , A. D. The asymmetric synthesis of β-haloaryl-β-amino acid derivatives . Synlett 2000 , 9 , 1257 – 1260 ; (b) Rosenthal , D. ; Brandrup , G. ; Davis , K. H. ; Wall , M. E. The synthesis of β-amino mercaptans and β-amino thiosulfates via ethylenimine intermediates . J. Org. Chem. 1965 , 30 , 3689 – 3696 .
  • (a) Loh , T. P. ; Wei , L. L. Indium trichloride–catalyzed conjugate addition of amines to α,β-ethylenic compounds in water. Synlett 1998, 9, 975–976; (b) Srivastava , N. ; Banik , B. K. Bismuth nitrate–catalyzed versatile Michael reactions. J. Org. Chem. 2003, 68, 2109–2114; (c) Wabnitz , T. C. ; Spencer , J. B. Convenient synthesis of Cbz-protected β-amino ketones by a copper-catalyzed conjugate addition reaction. Tetrahedron Lett. 2002, 43, 3891–3894; (d) Varala , R. ; Alam , M. M. ; Adapa , S. R. Chemoselective Michael-type addition of aliphatic amines to α,β-ethylenic compounds using bismuth triflate catalyst. Synlett 2003, 5, 720–722; (e) Azizi , N. ; Saidi , M. R. LiClO4-accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions. Tetrahedron 2004, 60, 383–387; (f) Bartoli , G. ; Bosco , M. ; Marcantoni , E. ; Petrini , M. ; Sambri , L. ; Torregiani , E. Conjugate addition of amines to α,β-enones promoted by CeCl3·7H2O–NaI system supported in silica gel. J. Org. Chem. 2001, 66, 9052–9055.
  • (a) Das , S. ; Borah , R. ; Devi , R. R. ; Thakur , A. J. Molecular iodine in protection and deprotection chemistry . Synlett 2008 , 18 , 2741 – 2762 ; (b) Deka , N. ; Kalita , D. J. ; Borah , R. ; Sarma , J. C. Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes . J. Org. Chem. 1997 , 62 , 1563 – 1564 ; (c) Kalita , D. J. ; Borah , R. ; Sarma , J. C. A new selective catalytic acetalization method promoted by microwave irradiation . Tetrahedron Lett. 1998 , 39 , 4573 – 4574 .
  • (a) Zhang , H. ; Zhang , Y. ; Liu , L. ; Xu , H. ; Wang , Y. RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles . Synthesis 2005 , 13 , 2129 – 2136 ; (b) Heiniger , S. A cupric acetate–catalyzed monocyanoethyllation of aromatic amines . J. Org. Chem. 1957 , 22 , 1213 – 1217 ; (c) Merchant , J. R. ; Chothia , D. S. Reactions of nitriles, part VIII: Synthesis of 2,3-dihydroquinoline-4(1H)-ones . J. Chem. Soc., Perkin Trans. 1 1972 , 932 – 935 ; (d) Ranu , B. C. ; Dey , S. S. ; Hajra , A. Solvent-free, catalyst-free Michael-type addition of amines to electron-deficient alkenes . Arkivoc 2002 , 7 , 76 – 81 ; (e) Amore , K. M. ; Leadbeater , N. E. ; Miller , T. A. ; Schmink , J. R. Fast, easy, solvent-free, microwave-promoted Michael addition of anilines to α,β-unsaturated alkenes: Synthesis of N-aryl functionalized β- amino esters and acids . Tetrahedron Lett. 2006 , 47 , 8583 – 8586 ; (f) Liu , B. K. ; Wu , Q. ; Qian , X. Q. ; Lv , D. S. ; Lin , X. F. N-Methylimidazole as a promising catalyst for the aza-Michael addition reaction of N-heterocycles . Synthesis 2007 , 17 , 2653 – 2559 ; (g) Zou , B. ; Jiang , H.-F. Synthesis of β-amino acids via catalyst and solvent-free Michael reaction . Chin. J. Chem. 2008 , 26 , 1309 – 1314 .

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.