Application of cyanophosphates in organic synthesis. Reactivity of. ALPHA.-cyano-. ALPHA.-diethylphosphonooxy anions.

T KURIHARA, K SANTO, S HARUSAWA…

Index: Kurihara, Takushi; Santo, Kazunori; Harusawa, Shinya; Yoneda, Ryuji Chemical and Pharmaceutical Bulletin, 1987 , vol. 35, # 12 p. 4777 - 4788

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Citation Number: 22

Abstract

The utility of the cyanohydrin diethylphosphates derived from aldehydes (arylaldehydes, crotonaldehyde, and cinnamaldehyde) as an acyl anion equivalent was examined. Deprotonation of cyanophosphates with n-butyllithium in the presence of tetramethylethylenediamine in tetrahydrofuran at-78° C followed by reactions with alkyl (acyl) halides, carbonyl compounds, and α, β-unsaturated nitriles or esters, as well as ...