Reactions of α,β-Unsaturated Ketone Acetals with Trimethylsilyl Cyanide and Trimethylsilyl Sulfides

DOI: 10.1246/bcsj.64.1108

Source and publish data:

Bulletin of the Chemical Society of Japan p. 1108 - 1117 (1991)

Update date:2022-08-04

Topics: Regioselectivity Column chromatography Yield NMR spectroscopy Nucleophilic addition TLC (thin-layer chromatography) Protecting group solvent-free conditions Michael addition Anhydrous conditions Silyl enol ether Workup Stereoselectivity Lewis Acid Catalyst Cyanohydrin Formation Mechanistic study Inert atmosphere

Authors:

Soga, Tsunehiko

Takenoshita, Haruhiro

Yamada, Masaaki

Han, Jeng S.

Mukaiyama, Teruaki

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Article abstract of DOI:10.1246/bcsj.64.1108

In the presence of a catalytic amount of trityl perchlorate, trimethylsilyl cyanide reacts with the dimethyl acetals of chalcone derivatives, with simultaneous double bond isomerization, to yield γ-methoxy-α,β-unsaturated carbonitriles.Trimethylsilyl sulf

Full text of DOI:10.1246/bcsj.64.1108

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