THE SYNTHESIS AND SOME MANIPULATIONS OF DIALKYL 6-ARYL (OR ALKYL)-2-OXOTETRAHYDRO-2H-PYRAN-3,5-DICARBOXYLATES

Authors
LAWRENCE RM PERLMUTTER P
Citation
Rm. Lawrence et P. Perlmutter, THE SYNTHESIS AND SOME MANIPULATIONS OF DIALKYL 6-ARYL (OR ALKYL)-2-OXOTETRAHYDRO-2H-PYRAN-3,5-DICARBOXYLATES, Australian Journal of Chemistry, 49(8), 1996, pp. 839-845
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Australian Journal of Chemistry → ACNP
ISSN journal
00049425
Volume
49
Issue
8
Year of publication
1996
Pages
839 - 845
Database
ISI
SICI code
0004-9425(1996)49:8<839:TSASMO>2.0.ZU;2-7
Abstract
A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl) malonate to alkyl 2-(1-hydroxy alkyl)propenoates, produces a mixture of dialkyl 6-aryl(or lkyl)-2-oxo tetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsatura tion into these molecules is also described.