Polylithiation of thioethers: a versatile route for polyanionic synthons

M Yus, A Gutiérrez, F Foubelo

Index: Yus, Miguel; Gutierrez, Ana; Foubelo, Francisco Tetrahedron, 2001 , vol. 57, # 20 p. 4411 - 4422

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Citation Number: 24

Abstract

The successive reaction of phenyl vinyl thioether (1) with n-butyllithium and an electophile [E1= PhCHO,(CH2) 4CO,(CH2) 5CO] in THF at− 78° C gives, after hydrolysis, the expected methylenic hydroxy thioethers (2). Deprotonation of 2 with n-butyllithium followed by a DTBB- catalysed lithiation and reaction with a second electrophile [E2= tBuCHO, PhCHO, Me2CO,(CH2) 5CO], at− 78° C, gives after hydrolysis the corresponding methylenic diols ...