Stereoselective syntheses of heterocycles via metallated alkoxyallenes

n-Butyllithium smoothly deprotonates alkoxyallenes at C-1. The generated lithiated species reacts with a variety of electrophiles furnishing after cyclization functionalized furan, pyrrole, or 1,2-oxazine derivatives. The formation of new C­C bonds often occurs with high stereoselectivities, which a...

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Bibliographic Details
Published inPure and applied chemistry Vol. 74; no. 1; pp. 175 - 180
Main Authors Reissig, Hans-Ulrich, Schade, Wolfgang, Okala Amombo, G. Marlyse, Pulz, Robert, Hausherr, Arndt
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.01.2002
Walter de Gruyter GmbH
Subjects
Butyllithium
Natural products
Stereoselectivity
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Summary:n-Butyllithium smoothly deprotonates alkoxyallenes at C-1. The generated lithiated species reacts with a variety of electrophiles furnishing after cyclization functionalized furan, pyrrole, or 1,2-oxazine derivatives. The formation of new C­C bonds often occurs with high stereoselectivities, which are exploited for efficient and selective syntheses of natural products or other compounds of interest.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200274010175