SYNTHESIS OF (E)-4-OXO-5-HEXENALS AND THEIR ACETAL DERIVATIVES

An effective synthesis of (E)-4-oxo-5-hexenals 6 and the acetals 5 starting from ethyl 2-alkoxy-1-cyclopropanecarboxylates 1 a-d is presented. The acid-induced ring opening of the cyclopropanecarboxylates 1 a, b followed by phosphorylmethylation or the phosphorylmethylation of the ester 1 c followed...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 12; pp. 1167 - 1169
Main Authors KANEMASA, S, OTSUKA, T, DOI, K, TSUGE, O, WADA, E
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1990
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
LITHIUM
FUNCTIONALIZED NITRILE OXIDE
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Summary:An effective synthesis of (E)-4-oxo-5-hexenals 6 and the acetals 5 starting from ethyl 2-alkoxy-1-cyclopropanecarboxylates 1 a-d is presented. The acid-induced ring opening of the cyclopropanecarboxylates 1 a, b followed by phosphorylmethylation or the phosphorylmethylation of the ester 1 c followed by ring opening leads to the 5-acetal of 2,5-dioxopentylphosphonate 4. The Horner-Emmons olefination of 4 with various aldehydes produces the title compounds.
ISSN:0039-7881
DOI:10.1055/s-1990-27125