Diastereoselective electrophilic substitution of γ-oxy-substituted benzyllithiums

✍ Scribed by Maria A Arrica; Ugo Azzena; Luciano Pilo; Elisabetta Piras

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 60 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00989-9

✦ Synopsis

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 CO 2 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.