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Facile synthesis of β-alkyl-substituted esters from α,β-unsaturated aldehydes

✍ Scribed by Tsujiaki Hata; Masashi Nakajima; Mitsuo Sekine

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
210 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

8-Alkyl-substituted carboxylates were synthesized in good yields from U,B-unsaturated aldehydes by using the 1:l carbonyl adducts with diethyl bis(trimethylsily1) phosphite. Recently, several studies on acyl anion equivalents utilizing carbonyl insertion reactions have appeared. 2 It has been reported that diethyl trimethylsilyl phosphite (DTSP) reacted with aldehydes to give 1:l carbonyl adducts in high yields. 3,4,5 In a previous paper5, we proposed cl-trimethylsilyloxybenzylphosphonate anion as a new benzoyl anion equivalent for the unsymmetrical ketone synthesis.

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Direct alkylation of α,β - unsaturated a
Direct alkylation of α,β - unsaturated aldehydes
✍ S.A.G. de Graaf; P.E.R. Oosterhoff; A. van der Gen 📂 Article 📅 1974 🏛 Elsevier Science 🌐 French ⚖ 181 KB

Alkylation of aldehydes, as a rule. requires transformation into intermediates such as enamines, to prevent base-catalysed condensations'. Only recently a direct alkylation with the aid of a phase-transfer catalyst, of aldehydes with a single a-hydrogen atom, was describedL. To our knowledge, the di