Reductive opening of 2-phenyl-1, 3-dioxolanes by a naphthalene-catalysed lithiation: synthetic applications

JF Gil, DJ Ramón, M Yus

Index: Gil, Juan F.; Ramon, Diego J.; Yus, Miguel Tetrahedron, 1993 , vol. 49, # 42 p. 9535 - 9546

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Citation Number: 39

Abstract

The reaction of 2-phenyl-1, 3-dioxolanes 1a, b with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol%) in tetrahydrofuran at− 40° C followed by successive reaction with an electrophile and final hydrolysis with water at the same temperature yields the corresponding monoprotected 1, 2-diols 2aa-2bf. The same process but allowing to rise the temperature to 20° C before the hydrolysis affords ...