The Journal of Organic Chemistry

Methoxy (phenylthio)(trimethylsilyl) methane as a one-carbon homologation reagent: efficient 1, 4-addition of a formyl or a carboxy anion equivalent to cyclic. alpha.- …

J Otera, Y Niibo, H Nozaki

Index: Otera, Junzo; Niibo, Yoshihisa; Nozaki, Hitosi Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5003 - 5007

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Citation Number: 24

Abstract

Efficient 1, 4-addition of a formyl and carboxy anion equivalent is realized by use of [methoxy (phenyl-thio)(trimethylsilyl) methyl] lithium. Of further synthetic value is consecutive a- alkylation by in situ trapping of intermediary enolates with various alkyl halides. The reaction proceeds highly regioselectively, thus no d-isomers are formed, and highly stereoselectively, thus trans a, &diallrylation products of more than 95% purity are formed. The unique ...