Catalytic direct-type substitution reaction of alpha-alkyl enolates: a Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates.
A mild and efficient process for the direct-type catalytic allylation of sulfonylimidates has been developed; this reaction represents the first example of Brønsted base-catalysed, in situ generation and use of alpha-alkyl enolates in substitution reactions; the success of this methodology stems from the tunable alpha-proton acidity and nucleophilicity of sulfonylimidates, which could be harnessed in the realization of a broader range of catalytic direct-type reactions using ester equivalents as nucleophiles.
Kan
S B Jennifer
SB
Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
Matsubara
Ryosuke
R
Berthiol
Florian
F
Kobayashi
Shū
S
D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D007096:Imidoesters / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*; D014961:X-Ray Diffraction; D047391:alpha-Cyclodextrins / Q000737:chemistry
D002264:Carboxylic Acids; D007096:Imidoesters; D013450:Sulfones; D047391:alpha-Cyclodextrins; D010165:Palladium; C032613:alpha-cyclodextrin