Cu(acac)2 Immobilized in Ionic Liquids: A Recoverable and Reusable Catalytic System for Aza‐Michael Reactions

Copper(II) acetylacetonate immobilized in ionic liquids efficiently catalyzes the aza-Michael reaction of amines with α,β-unsaturated carbonyl compounds to produce the corresponding β-amino carbonyl compounds with great alacrity in excellent yields. The reactions are far more facile than those reported earlier. The recovered ionic liquid phase containing the copper catalyst can be reused for several cycles with consistent activity.

[1]  C. Xia,et al.  Transition‐Metal‐Based Lewis Acid Catalysis of Aza‐Type Michael Additions of Amines to α,β‐Unsaturated Electrophiles in Water , 2004 .

[2]  Shaolin Zhou,et al.  A green, ionic liquid and quaternary ammonium salt-catalyzed aza-Michael reaction of α,β-ethylenic compounds with amines in water , 2004 .

[3]  M. Kantam,et al.  Cu(acac)2 Immobilized in Ionic Liquids: A Novel and Recyclable Catalytic ­System for Aziridination of Olefins Using PhI=NTs as Nitrene Donor , 2004 .

[4]  N. Azizi,et al.  LiClO4 Accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions , 2004 .

[5]  Shaolin Zhou,et al.  Efficient Copper-Catalyzed Chemo Selective Conjugate Addition of Aliphatic Amines to α,β-Unsaturated Compounds in Water , 2003 .

[6]  C. Xia,et al.  An efficient and inexpensive catalyst system for the aza-Michael reactions of enones with carbamates. , 2003, Chemical communications.

[7]  J. Yadav,et al.  Aza-Michael Reactions in Ionic Liquids. A Facile Synthesis of β-Amino Compounds , 2003 .

[8]  J. Snyder,et al.  Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes: A novel, stereoselective synthesis of α, β-disubstituted β-amino carbonyl compounds via chiral auxiliary mediated azetine formation , 2003 .

[9]  B. Banik,et al.  Bismuth nitrate-catalyzed versatile Michael reactions. , 2003, The Journal of organic chemistry.

[10]  M. Snapper,et al.  Multiple component reactions: an efficient nickel-catalyzed Reformatsky-type reaction and its application in the parallel synthesis of beta-amino carbonyl libraries. , 2003, The Journal of organic chemistry.

[11]  S. Fustero,et al.  New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids , 2002 .

[12]  C. Gordon New developments in catalysis using ionic liquids , 2001 .

[13]  E. Marcantoni,et al.  Conjugate Addition of Amines to α,β-Enones Promoted by CeCl3·7H2O−NaI System Supported in Silica Gel , 2001 .

[14]  R. Sheldon Catalytic reactions in ionic liquids. , 2001, Chemical communications.

[15]  R. Kazlauskas,et al.  Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations. , 2001, The Journal of organic chemistry.

[16]  A. Bedekar,et al.  Clay catalyzed chemoselective Michael type addition of aliphatic amines to α,β-ethylenic compounds , 2001 .

[17]  P. Wasserscheid,et al.  Ionic Liquids-New "Solutions" for Transition Metal Catalysis. , 2000, Angewandte Chemie.

[18]  E. Corey,et al.  Highly enantioselective Michael reactions catalyzed by a chiral quaternary ammonium salt. Illustration by asymmetric syntheses of (S)-ornithine and chiral 2-cyclohexenones. , 2000, Organic letters.

[19]  T. Loh,et al.  Indium Trichloride-Catalyzed Conjugate Addition of Amines to α,β-Ethylenic Compounds in Water , 1998 .

[20]  Michael Arend,et al.  Modern Variants of the Mannich Reaction. , 1998, Angewandte Chemie.

[21]  E. Corey,et al.  A Novel Chiral Super-Lewis Acidic Catalyst for Enantioselective Synthesis , 1996 .

[22]  P. Suarez,et al.  The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes , 1996 .

[23]  S. Davies,et al.  An Asymmetric Synthesis of N-Protected β-Amino Aldehydes and β-Amino Ketones , 1995 .

[24]  N. Lydon,et al.  [(Alkylamino)methyl]acrylophenones: potent and selective inhibitors of the epidermal growth factor receptor protein tyrosine kinase. , 1995, Journal of medicinal chemistry.

[25]  G. Jenner Catalytic high pressure synthesis of hindered β-aminoesters , 1995 .

[26]  E. Marcantoni,et al.  Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters , 1994 .

[27]  Li Xiaomei,et al.  THE MANNICH REACTION OF CYCLIC KETONES, AROMATIC ALDEHYDES AND AROMATIC AMINES , 1991 .

[28]  E. Eliel,et al.  Highly stereoselective syntheses involving N-alkyl-4,4,7.alpha.-trimethyl-trans-octahydro-1,3-benzoxazine intermediates. 2. , 1990 .

[29]  M. Ohno,et al.  Stereocontrolled synthesis of (+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction , 1982 .

[30]  C. Tomasini,et al.  Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids , 1996 .

[31]  H. Natsugari,et al.  Stereoselective synthesis of sperabillins and related compounds , 1991 .

[32]  E. Corey,et al.  Enantioselective and practical syntheses of R- and S-fluoxetines , 1989 .