Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles

A new efficient gold(III) catalysed synthesis of β-enaminones from 1,3-dicarbonyl compounds and ammonia/amines providing an attractive and environmental friendly alternative to the more vigorous reagents and drastic conditions of the existing methodologies is described; the catalysis of gold(III) is also extended to reaction of cyclic 1,3-dicarbonyls with O-, P- and S-nucleophiles.

[1]  A. Navarro‐Vázquez,et al.  A study of aryl radical cyclization in enaminone esters. , 2002, The Journal of organic chemistry.

[2]  O. Attanasi,et al.  Sequential base-promoted annulation/ palladium-catalyzed domino 1,5-enyne arylation and vinylation of alpha-propargylaminohydrazones. , 2002, Angewandte Chemie.

[3]  J. Bats,et al.  Homogeneous gold-catalyzed synthesis of biphenyls and furfuryl-substituted arenes , 2002 .

[4]  E. Rossi,et al.  Conversion of homochiral amines and α-amino esters to their chiral 1,2,3,5-substituted pyrrole derivatives via gold-catalysed amination/annulation reactions of 2-propynyl-1,3-dicarbonyl compounds , 2001 .

[5]  E. Rossi,et al.  Gold-Catalyzed Sequential Amination/Annulation Reactions of 2-Propynyl-1,3-dicarbonyl Compounds , 2001 .

[6]  M. Chiarini,et al.  Sequential alkylation/transition metal catalysed annulation reactions of 1,3-dicarbonyl compounds with propargyl bromide , 2000 .

[7]  Pietro Tundo,et al.  Synthetic pathways and processes in green chemistry. Introductory overview , 2000 .

[8]  J. Ellman,et al.  One-pot asymmetric synthesis of tert-butanesulfinyl-protected amines from ketones by the in situ reduction of tert-butanesulfinyl ketimines , 1999 .

[9]  A. Zapata,et al.  Synthesis of Enaminones Using Trimethylsilyl Trifluoromethanesulfonate as an Activator. , 1997 .

[10]  C. Sehon,et al.  Synthesis of Furans and 2,5-Dihydrofurans by Ag(I)-Catalyzed Isomerization of Allenones, Alkynyl Allylic Alcohols, and Allenylcarbinols , 1995 .

[11]  J. Hamelin,et al.  Synthesis in dry media coupled with microwave irradiation : Application to the preparation of enaminoketones. , 1993 .

[12]  C. Kowalski,et al.  Enone mesylates. Precursors to .beta.-substituted cyclohexenones , 1981 .

[13]  F. Westheimer,et al.  Catalysis by molecular sieves in the preparation of ketimines and enamines , 1971 .

[14]  D. F. Martin,et al.  Stabilities of Bivalent Metal Complexes of Some B-Ketoimines , 1961 .

[15]  J. Billman,et al.  Reduction of Schiff Bases. II. Benzhydrylamines and Structurally Related Compounds1a,b , 1958 .