An efficient and mild bismuth triflate-catalysed three-component Mannich-type reaction

Département de Chimie, Université Laval, Québec, Canada.
Organic & Biomolecular Chemistry (Impact Factor: 3.49). 11/2007; 5(19):3126-34. DOI: 10.1039/b710794c
Source: PubMed

ABSTRACT In the presence of a catalytic amount of Bi(OTf)(3).4H(2)O, aldehydes together with amines react with silyl enolates to afford the corresponding Mannich-type adducts smoothly. A wide variety of silyl enolates derived from ketones, as well as esters and thioesters, react rapidly to afford the beta-amino ketones or the beta-amino esters in high yields (up to 94%).

  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Keywords: Allylation / Bismuth / Lewis acids / Microwaves / Allyltin In the presence of a catalytic amount of bismuth triflate and under microwave irradiation, mixtures of aldehyde and allyl-stannane afforded smoothly the corresponding homoallylic alcohol. A wide variety of aldehydes were treated under these conditions. The reactions proceeded rapidly and af-forded smoothly the corresponding homoallylic alcohol in
    European Journal of Organic Chemistry 12/2007; DOI:10.1002/ejoc.200700817 · 3.15 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: In the presence of a catalytic amount of Bi(OTf)(3)-4H(2)O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could be obtained without aqueous work-up by simple filtration. (c) 2007 Published by Elsevier Ltd.
    Tetrahedron Letters 02/2008; 49(9):1546-1550. DOI:10.1016/j.tetlet.2007.12.100 · 2.39 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: The direct alkylation of silyl enol ethers with para-methoxybenzylic alcohols or their corresponding acetates was efficiently catalyzed by Bi(OTf)3 in CH3NO2 as the solvent. The reaction provided the α-benzylated carbonyl compounds in high yields after short reaction times using 1–2.5mol% of the catalyst. Benzylic acetates other than para-methoxybenzylic acetates also underwent the reaction. High facial diastereoselectivities were observed with acetates derived from chiral α-branched para-methoxybenzylic alcohols. In addition, a catalytic reduction with Et3SiH as the reducing agent is reported.
    Tetrahedron Letters 02/2008; 49(8):1305-1309. DOI:10.1016/j.tetlet.2007.12.092 · 2.39 Impact Factor