New masked δ-lithiocarbonyl compounds: preparation and synthetic applications

JF Gil, DJ Ramón, M Yus

Index: Gil, Juan F.; Ramon, Diego J.; Yus, Miguel Tetrahedron, 1993 , vol. 49, # 22 p. 4923 - 4938

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Citation Number: 47

Abstract

The reaction of 2-(4-chlorobutyl)-1, 3-dioxolanes (1a–c) or 2-(4-chlorobutyl)-2-ethyl-1, 3- dithiane (1d) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol%) in THF at-78° C leads to a solution of the corresponding masked lithium δ-enolates 2, which react with different electrophiles (water, deuterium oxide, carbonyl compounds, carboxylic acid derivatives, dibenzyl disulfide or benzylideneaniline) to yield the expected ...