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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 6
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Original Articles

Zirconium(IV) Chloride–Mediated Chemoselective Conjugate Addition of Aliphatic Amines to α,β‐Ethylenic Compounds

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Pages 795-801 | Received 01 Sep 2005, Published online: 16 Aug 2006

References

  • Arend , M. , Westermann , B. and Risch , N. 1998 . Modern variants of the Mannich reaction . Angew. Chem., Int. Ed. Engl. , 37 : 1044 – 1070 .
  • Cardillo , G. and Tomasini , C. 1996 . Asymmetric synthesis of β‐amino acids and α‐substituted β‐amino acids . Chem. Soc. Rev. , : 117 – 128 .
  • Shaikh , N. S. , Deshpande , V. H. and Bedekar , A. V. 2001 . Clay‐catalyzed chemoselective Michael‐type addition of aliphatic amines to α,β‐ethylenic compounds . Tetrahderon , 57 : 9045 – 9048 .
  • Azizi , N. and Saidi , M. 2004 . LiClO4 accelerated Michael addition of amines to α,β‐unsaturated olefins under solvent‐free conditions . Tetrahedron , 60 : 383 – 387 .
  • Jenner , G. 1995 . Catalytic high‐pressure synthesis of hindered β‐amino esters . Tetrahedron Lett. , 36 : 233 – 236 .
  • D'Angelo , J. and Maddaluno , J. 1986 . Enantioselective synthesis of β‐amino esters through high‐pressure‐induced addition of amines to α,β‐ethylenic esters . J. Am. Chem. Soc. , 108 : 8112 – 8117 .
  • Loh , T. P. and Wei , L. L. 1998 . Indium trichloride–catalyzed conjugate addition of amines to α,β‐ethylenic compounds in water . Synlett , : 975 – 976 .
  • Kawatsura , M. and Hartwig , J. F. 2001 . Transition metal–catalyzed addition of amines to acrylic acid derivatives. A high‐throughput method for evaluating hydroamination of primary and secondary alkylamines . Organometallics , 20 : 1960
  • Srivastava , N. and Banik , B. K. 2003 . Bismuth nitrate–catalyzed versatile Michael reactions . J. Org. Chem. , 68 : 2109 – 2114 .
  • Varala , R. , Alam , M. M. and Adapa , S. R. 2003 . Chemoselective Michael‐type addition of aliphatic amines to α,β‐ethylenic compounds using bismuth triflate catalyst . Synlett , : 720
  • Evans , D. A. , Chapman , K. T. and Bisaha , J. 1988 . Asymmetric Diels–Alder cycloaddition reactions with chiral α,β‐unsaturated N‐acyloxazolidinones . J. Am. Chem. Soc. , 110 : 1238 – 1256 .
  • Phillipson , N. , Anson , M. S. , Montana , J. G. and Taylor , R. J. K. 1997 . Ketone homologation to produce α‐methoxyketones: application to conduritol synthesis . J. Chem. Soc., Perkin. Trans. 1 , 19 : 2821 – 2829 .
  • Lenarsic , R. , Kocevar , M. and Polane , S. 1999 . ZrCl4‐mediated regioselective electrophilic amination of activated arenes with new alkyl arylaminocarbonyldiazenecarboxylates: intermolecular and intramolecular reactions . J. Org. Chem. , 64 : 2558 – 2563 .
  • Carroll , M. A. , Widdowson , D. A. and Williams , D. J. 1994 . A short efficient route to c2 symmetric 1,1′‐2,2′‐tetrasubstituted ferrocenes . Synlett. , 11 : 1025 – 1026 .
  • Harrowven , D. C. and Dainty , R. F. 1996 . Zirconium tetrachloride as a mediator for ambient temperature ortho‐fries rearrangements . Tetrahedron Lett. , 37 : 7659 – 7660 .
  • Yadav , J. S. , Reddy , B. V.S. , Raj , K. S. , Reddy , K. B. and Prasad , A. R. 2001 . Zr+4‐catalyzed efficient synthesis of α‐aminophosphonates . Synthesis , 15 : 2277 – 2280 .
  • Meshram , H. M. , Premalatha , K. , Rameshbabu , K. , Eeshwaraiah , B. and Yadav , J. S. 2004 . Zirconium(IV) chloride catalyzed cyclization of ortho‐allyphenols: synthesis of 2‐methyl‐2,3‐dihydrobenzofurans . Syn. Commun. , 34 : 1 – 6 .

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