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The ester dienolate [2,3]-Wittig rearrangement. Diastereoselective synthesis of 2,3-dialkenyl-substituted 2-hydroxy-γ-lactones

✍ Scribed by Martin Hiersemann

Book ID
104209234
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
928 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The ester dienolate [2,3]-Wittig rearrangement proceeds with high yield and anti/syn diastereoselection to afford 3-alkoxycarbonyl-3-hydroxy-substituted 1,5-hexadienes. No donor solvent or metal salt additive was necessary to trigger the rearrangement. The rearrangement product was transformed to diastereomerically pure 2,3-dialkenyl-substituted y-lactones. A transition state picture was proposed based on previously reported transition state models for enolate [2,3]-Wittig rearrangements.

📜 SIMILAR VOLUMES

ChemInform Abstract: The Dienolate [2,3]
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