Alkylation of acetals using manganate-BF3-OEt2 mixed reagent

A mixture of 'R3MnMgBr' and BF3.OEt2 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' t...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 23; pp. 4499 - 4501
Main Authors Hojo, M, Ushioda, N, Hosomi, A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 31.05.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Lewis acid
KETONES
acetal
COPPER-CATALYZED 1,4-ADDITION
ketal
alkylation
GENERATION
ORGANOMANGANESE(II) REAGENTS
manganese
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Summary:A mixture of 'R3MnMgBr' and BF3.OEt2 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. alpha-Alkoxy-substituted cyclic ethers and acetoxy- substituted cyclic ethers were selectively converted to ring-opening alkylation products and alpha-alkyl-substituted cyclic ethers, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2004.04.050