Reductive lithiation of diastereoisomeric mixtures of 4-aryl-5-methyl-1,3-dioxanes occurs with epimerization at the benzylic centre. Reaction of intermediate organometals with alkyl halides or CO2 afforded 2-methyl-3-substituted-3-phenylpropan-1-ols, or the corresponding lactones, with satisfactory yields and satisfactory to high diastereoselectivities. Observed diastereoselectivities strongly depend on the substitution pattern of starting materials.

Diastereoselective Electrophilic Substitution of g-Oxy-Substituted Benzyllithiums", Tetrahedron Letters, 43, 5137-5139 (2002) / MARIA ANTONIETTA, Arrica; Azzena, Ugo Gavino; Luciano, Pilo; Elisabetta, Piras. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 43:(2002), pp. 5137-5139. [10.1016/S0040-4039(02)00989-9]

Diastereoselective Electrophilic Substitution of g-Oxy-Substituted Benzyllithiums", Tetrahedron Letters, 43, 5137-5139 (2002)

AZZENA, Ugo Gavino;
2002-01-01

Abstract

Reductive lithiation of diastereoisomeric mixtures of 4-aryl-5-methyl-1,3-dioxanes occurs with epimerization at the benzylic centre. Reaction of intermediate organometals with alkyl halides or CO2 afforded 2-methyl-3-substituted-3-phenylpropan-1-ols, or the corresponding lactones, with satisfactory yields and satisfactory to high diastereoselectivities. Observed diastereoselectivities strongly depend on the substitution pattern of starting materials.
2002
Diastereoselective Electrophilic Substitution of g-Oxy-Substituted Benzyllithiums", Tetrahedron Letters, 43, 5137-5139 (2002) / MARIA ANTONIETTA, Arrica; Azzena, Ugo Gavino; Luciano, Pilo; Elisabetta, Piras. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 43:(2002), pp. 5137-5139. [10.1016/S0040-4039(02)00989-9]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/45517
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