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Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates

Citation

Moorhoff, CM, Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates, Tetrahedron, 53, (6) pp. 2241-2252. ISSN 0040-4020 (1997) [Refereed Article]

DOI: doi:10.1016/S0040-4020(96)01126-X

Abstract

Novel Michael-Wittig condensations of methyl 3-oxo-4-(triphenylarsoranylidene)-butanoate 6 and substituted 2,2-dimethyl-2H-pyran-5-carboxylates 5a to 5e gave substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8a to 8e in a mixture of three keto diastereomers and two enol diastereomers. Apart from substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8f to 8g, less hindered substituted 2-methyl-2H-pyran-5-carboxylates 5f and 5g gave the substituted tetrahydrobenzofurans 9f and 9g. 4-Halomethyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8 were mostly in the enol diastereomeric form. A plausible mechanism is given for the unique formation for these products.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Moorhoff, CM (Dr Moorhoff)
ID Code:11994
Year Published:1997
Web of Science® Times Cited:17
Deposited By:Chemistry
Deposited On:1997-08-01
Last Modified:2011-08-15
Downloads:0

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