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Synthesis 1999; 1999(4): 664-668
DOI: 10.1055/s-1999-3442
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Generation of γ-Oxy-Substituted Benzylithium Derivatives by Reductive Lithiation of 4-Phenyl-1,3-dioxanes

Ugo Azzena* , Luciano Pilo
  • *Dipartimento di Chimica, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy; Fax +39(79)22 95 59; E-mail: ugo@ssmain.uniss.it
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Publication Date:
31 December 1999 (online)

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Reductive cleavage of 1,3-dioxanes 1a-c with Li metal in the presence of a catalytic amount of naphthalene in THF, followed by reaction with different electrophiles, allowed the synthesis of 3-substituted- and 3,3-disubstituted-3-phenylpropan-1-ols 4 in good yields.

acetals - reduction - lithiation - carbanions - electron transfer

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