Alkylation of acetals using manganate–BF 3·OEt 2 mixed reagent

A mixture of `R 3MnMgBr' and BF 3·OEt 2 in ether converted acetals and ketals to alkylation products. A mixture of `R 3MnMgBr' and BF 3·OEt 2 prepared in advance only by stirring both reagents in ether converted acetals to alkylation products, where an alkoxy group of acetals was substitut...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 23; pp. 4499 - 4501
Main Authors Hojo, Makoto, Ushioda, Nobuo, Hosomi, Akira
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2004
Subjects
Acetal
Alkylation
Ketal
Lewis acid
Manganese
Lewis acid
Acetal
Ketal
Alkylation
Manganese
Online AccessGet full text

Cover

More Information
Summary:A mixture of `R 3MnMgBr' and BF 3·OEt 2 in ether converted acetals and ketals to alkylation products. A mixture of `R 3MnMgBr' and BF 3·OEt 2 prepared in advance only by stirring both reagents in ether converted acetals to alkylation products, where an alkoxy group of acetals was substituted by the alkyl group of manganese reagent used. Ketals also reacted with the `mixed reagent' to afford the corresponding alkylation products in high yield. α-Alkoxy-substituted cyclic ethers and acetoxy-substituted cyclic ethers were selectively converted to ring-opening alkylation products and α-alkyl-substituted cyclic ethers, respectively.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.04.050