The synthesis and some manipulations of dialkyl 6-aryl (or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates

A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl) malonate to alkyl 2-(1-hydroxyalkyl)propenoates, produces a mixture of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be h...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 49; no. 8; pp. 839 - 845
Main Authors Lawrence, RM, Perlmutter, P
Format Journal Article
LanguageEnglish
Published COLLINGWOOD C S I R O PUBLICATIONS 01.01.1996
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
KETONES
CONVERSION
ACIDS
SYN ELIMINATION
ESTERS
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Summary:A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl) malonate to alkyl 2-(1-hydroxyalkyl)propenoates, produces a mixture of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsaturation into these molecules is also described.
ISSN:0004-9425
DOI:10.1071/CH9960839