Electrogenerated acid-catalyzed reactions of acetals, aldehydes, and ketones with organosilicon compounds, leading to aldol reactions, allylations, cyanations, and …

…, S Takagishi, H Horike, H Kuroda, K Uneyama

Index: Torii, Sigeru; Inokuchi, Tsutomu; Takagishi, Sadahito; Horike, Hirofumi; Kuroda, Hideki; Uneyama, Kenji Bulletin of the Chemical Society of Japan, 1987 , vol. 60, p. 2173 - 2188

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Citation Number: 39

Abstract

Exquisite use of electrogenerated acid (EG acid) in the silicon-mediated acid-catalyzed reactions; eg, aldol reactions, allylations, cyanations, and hydride additions is described. The aldol reaction of acetals 1 with enol trimethylsilyl ethers 3 and 1, 2-bis (trimethylsiloxy) alkenes 4 gives the corresponding adducts 5 and 6, respectively. The reaction proceeds smoothly with EG acid derived from perchlorate salts such as LiClO 4, n-Bu 4 NClO 4, and ...