Synthesis of Substitutedα-(Hydroxymethyl)-β-iodoacrylatesvia MgI2-Promoted Stereoselective Aldol Coupling
| Autor: | Han-Xun Wei, Guigen Li, Richard L. Jasoni, Paul W. Paré, Jiali Hu |
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| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Reaction mechanism Stereochemistry Organic Chemistry Biochemistry Aldehyde humanities Catalysis Coupling reaction Adduct Inorganic Chemistry chemistry.chemical_compound Aldol reaction chemistry Drug Discovery Stereoselectivity Hydroxymethyl Lewis acids and bases Physical and Theoretical Chemistry |
| Zdroj: | Helvetica Chimica Acta. 87:2359-2363 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.200490212 |
| Popis: | The efficient and highly stereoselective syntheses of a variety of (Z)-configured, substituted α-(hydroxymethyl)-β-iodo-acrylates from prop-2-ynoate and various aldehydes was achieved. The synthetic protocol involves a simple one-pot coupling reaction under mild conditions, promoted by MgI2, which serves both as a Lewis acid and iodine source for a BaylisHillman-type reaction. All adducts were generated in good-to-excellent yields, the (Z)-isomers being formed in high selectivity (>98%). The conversion of methyl prop-2-ynoate into an active ‘β-iodo allenolate’ intermediate, which then nucleophilically attacks an aldehyde, is proposed as a plausible reaction mechanism. |
| Databáze: | OpenAIRE |
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