Vanadyl(IV) Acetate: An Efficient, Reusable Heterogenous Catalyst for Aza-Michael Reaction Under Solvent-Free Conditions

REFERENCES

• Perlmutter , P. Conjugate Addition Reaction in Organic Synthesis ; Pergamon Press : Oxford , 1992 ; p. 114 .
   Google Scholar
• ( a ) Wang , Y. F. ; Izawa , T. ; Kobayashi , S. ; Ohno , M. Stereocontrolled synthesis of (+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction . J. Am. Chem. Soc. 1982 , 104 , 6465 ; ( b ) Hashiguchi , S. ; Kawada , A. ; Natsugari , H. Stereoselective synthesis of sperabillins and related compounds . J. Chem. Soc., Perkin Trans. 1 1991 , 2435 ; ( c ) Senanayake , C. H. ; Fang , K. ; Grover , P. ; Bakale , R. P. ; Vandenbossche , C. P. ; Wald , S. A. Rigid aminoalcohol backbone as a highly defined chiral template for the preparation of optically active tertiary α-hydroxyl acids . Tetrahedron Lett. 1999 , 40 , 819 ; ( d ) Genov , M. ; Dimitrov , V. ; Ivanova , V. New δ-amino alcohol for the enantioselective addition of dialkylzincs to aldehydes . Tetrahedron: Asymmetry 1997 , 8 , 3703 ; ( e ) Eliel , E. L. ; He , X. Highly stereoselective syntheses involving N-alkyl-4,4,7a-trimethyl-tra-nosctahydro-1,3-benzoxazine in termediates . J. Org. Chem. 1990 , 55 , 2114 ; ( f ) Hattori , K. ; Miyata , M. ; Yamamoto , H. Highly selective and operationally simple synthesis of enantiomerically pure β-amino esters via double stereodifferentiation . J. Am. Chem. Soc. 1993 , 115 , 1151 ; ( g ) Hayashi , Y. ; Rode , J. J. ; Corey , E. J. A novel chiral super-Lewis acidic catalyst for enantioselective synthesis . J. Am. Chem. Soc. 1996 , 118 , 5502 .
   Web of Science ®Google Scholar
• Angelo , J. ; Maddaluno , J. J. Am. Chem. Soc. 1986 , 108 , 8112 .
   Google Scholar
• Cabral , J. ; Laszlo , P. ; Mahe , L. ; Montaufier , M. T. ; Randriamahefa , S. L. Catalysis of the specific Michael addition: The example of acrylate acceptors . Tetrahedron Lett. 1989 , 30 , 3969 .
   Google Scholar
• Matsubara , M. ; Yoshioka , M. ; Utimoto , K. Lanthanoid triflate–catalyzed conjugate addition of amines to α,β-unsaturated esters: A facile route to optically active β-lactam . Chem. Lett. 1994 , 827 .
   Google Scholar
• Jenner , G. Catalytic high pressure synthesis of hindered β-aminoesters . Tetrahedron Lett. 1995 , 36 , 233 .
   Web of Science ®Google Scholar
• Loh , T. P. ; Wei , L. L. Indium trichloride–catalyzed conjugate addition of amines to α,β-ethylenic compounds in water . Synlett. 1998 , 975 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Xu , L. W. ; Li , J. W. ; Xia , C. G. ; Zhou , S. L. ; Hu , X. X. Efficient copper-catalyzed chemo selective conjugate addition of aliphatic amines to α,β-unsaturated compounds in water . Synlett 2003 , 2425 .
   Google Scholar
• Srivastava , N. ; Banik , B. K. Bismuth nitrate–catalyzed versatile Michael reactions . J. Org. Chem. 2003 , 68 , 2109 .
   PubMed Web of Science ®Google Scholar
• 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 , 720 .
   Google Scholar
• Fadini , L. ; Togni , A. Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins . Chem. Commun. 2003 , 30 .
   Google Scholar
• Xu , L. W. ; Li , L. ; Xia , C. G. Transition-metal-based Lewis acid catalysis of aza-type Michael additions of amines to α,β-unsaturated electrophiles in water . Helv. Chim. Acta 2004 , 87 , 1522 .
   Google Scholar
• Azizi , N. ; Saidi , M. R. LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions. Tetrahedron 2004, 60, 383.
   Web of Science ®Google Scholar
• Kantam , M. L. ; Neeraja , V. ; Kavita , B. ; Neelima , B. ; Chaudhuri , M. K. ; Hussain , S. Cu(acac)2 immobilized in ionic liquids: A recoverable and reusable catalytic system for aza-Michael reactions . Adv. Synth. Catal. 2005 , 347 , 763 .
   Web of Science ®Google Scholar
• Chaudhuri , M. K. ; Hussain , S. ; Kantam , M. L. ; Neelima , B. Boric acid: A novel and safe catalyst for aza-Michael reactions in water . Tetrahedron Lett. 2005 , 46 , 8329 .
   Web of Science ®Google Scholar
• Hashemi , M. M. ; Eftekhari-Sis , B. ; Abdollahifar , A. ; Khalili , B. ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions . Tetrahedron 2006 , 62 , 672 .
   Web of Science ®Google Scholar
• Surendra , K. ; Krishnaveni , N. S. ; Sridhar , R. ; Rao , K. R. β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water . Tetrahedron Lett. 2006 , 47 , 2125 .
   Web of Science ®Google Scholar
• Duan , Z. ; Xuan , X. ; Li , T. ; Yang , C. ; Wu , Y. Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles . Tetrahedron Lett. 2006 , 47 , 5433 .
   Web of Science ®Google Scholar
• Vivek , P. R. ; Ramakrishna , P. B. ; Shriniwas , D. S. Polyvinyl pyridine as a novel solid heterogeneous, recyclable catalyst for aza-Michael reaction . Synlett 2006 , 2676 .
   Google Scholar
• Choudary , B. M. ; Kantam , M. L. ; Neeraja , V. ; Bandyopadhyay , T. ; Reddy , P. N. Vanadyl(IV) acetate, a new reusable catalyst for acetylation of alcohols . J. Mol. Catal. 1999 , 140 , 25 .
   Google Scholar
• Choudary , B. M. ; Neeraja , V. ; Kantam , M. L. Vanadyl(IV) acetate: A mild and efficient heterogeneous catalyst for the tetrahydropyranylation of alcohols, thiols, and phenols . J. Mol. Catal. 2001 , 175 , 169 .
   Google Scholar
• Kantam , M. L. ; Neeraja , V. ; Sreekanth , P. Vanadyl(IV) acetate: A mild and efficient catalyst for the deprotection of acetals and ketals . Catal. Commun. 2001 , 2 , 301 .
   Google Scholar
• Varala , R. ; Sreelatha , N. ; Adapa , S. R. Ceric ammonium nitrate–catalyzed aza-Michael addition of aliphatic amines to α,β-unsaturated carbonyl compounds and nitriles in water . Synlett 2006 , 1549 .
   Google Scholar