Radical reactions on enol-esters: facile synthesis of 3-ulosonic acid derivatives and chiral spiroacetals

A two-step approach to 3-ulosonic acid derivatives and chiral spiroacetals from enol-esters is presented. The strategy involves 1,4-addition of a variety of alcohols onto enol-esters in the presence of NBS to give α-bromoacetals, which undergo a regio- and stereoselective radical cyclisation to give...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 14; no. 19; pp. 2991 - 3004
Main Authors Sharma, G.V.M., Rakesh, Chander, A.Subhash, Reddy, V.Goverdhan, Rao, M.H.V.Ramana, Kunwar, A.C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.10.2003
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
LACTONES
MEDIATED STEREOSELECTIVE-SYNTHESIS
CYCLIZATION REACTIONS
ANALOGS
STRUCTURAL VARIATIONS
WITTIG OLEFINATION
ACETALS
C-GLYCOSIDES
N-ACETYLNEURAMINIC ACID
SPIROKETALS
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Summary:A two-step approach to 3-ulosonic acid derivatives and chiral spiroacetals from enol-esters is presented. The strategy involves 1,4-addition of a variety of alcohols onto enol-esters in the presence of NBS to give α-bromoacetals, which undergo a regio- and stereoselective radical cyclisation to give the highly functionalised chiral spiroacetals, while debromination gives 3-ulosonic acid derivatives. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(03)00448-8