Nucleophilic aminomethylation of aldehydes with. ALPHA.-amino alkylsilanes.

O Tsuge, J Tanaka, S Kanemasa

Index: Tsuge, Otohiko; Tanaka, Junji; Kanemasa, Shuji Bulletin of the Chemical Society of Japan, 1985 , vol. 58, # 7 p. 1991 - 1999

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Citation Number: 23

Abstract

Fluoride-induced desilylation of (α-phthalimido-, α-morpholino-, and α-acetamidobenzyl) silanes and a (phthalimidomethyl) silane generates the corresponding α-amino carbanions which add to a variety of aldehydes. The conversion of phthalimido group of the adducts into amino moiety leads to β-amino alcohols. This simple reaction sequence offers a new and general method of nucleophilic aminomethylation.