Reactions of a 3(2H)-furanone lithium enolate with 4-halocrotonates

Depending upon the solvent and reaction conditions, reactions of the lithium dienolate 2 with 4-halocrotonate esters 3 gave largely the simple alkylation product 4, a mixture of diastereomeric cyclopropyl esters 5, or the halo 7-oxabicycloheptanones 6.

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Bibliographic Details
Published inSynlett no. 9; pp. 1391 - 1394
Main Authors Caine, DS, Paige, MA
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.09.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
sequential Michael additions
4-halocrotonate
MICHAEL
alkylation
3(2H)-furanone dienolate
DERIVATIVES
Michael addition-cyclopropanation
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Summary:Depending upon the solvent and reaction conditions, reactions of the lithium dienolate 2 with 4-halocrotonate esters 3 gave largely the simple alkylation product 4, a mixture of diastereomeric cyclopropyl esters 5, or the halo 7-oxabicycloheptanones 6.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-1999-2864