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Neutral Coordinate‐Organocatalysts in Organic Synthesis: Allylation of Acylhydrazones with Allyltrichlorosilanes

Advanced Synthesis & CatalysisPublished 1 August 2004
Shū Kobayashi, Masaharu Sugiura, Chikako Ogawa
Citations96
SJR quartileQ1
SJR score0.93
SNIP0.92

Abstract

Abstract N,N ‐Dimethylformamide (DMF), sulfoxides, and phosphine oxides, etc., which are neutral, uncharged molecules and coordinate to silicon atoms of organosilicon reagents to activate nucleophilic addition, are defined as neutral coordinate‐organocatalysts (NCOs). In the presence of NCOs , allylation reactions of acylhydrazones, useful imine surrogates, using allyltrichlorosilanes proceed smoothly to afford the synthetically useful racemic and non‐racemic homoallylic amine derivatives in high yields with high diastereoselectivities.

Keywords

Chemistry