A new synthesis of β, γ-alkenyl carboxylic acids from α, β-alkenyl carboxylic acid chlorides and α, β-alkenyl aldehydes with one-carbon elongation

…, A Nakamura, A Iriuchijima, Y Hayashi, K Kubota

Index: Satoh, Tsuyoshi; Nakamura, Akira; Iriuchijima, Atsuko; Hayashi, Yasumasa; Kubota, Ko-Ichi Tetrahedron, 2001 , vol. 57, # 48 p. 9689 - 9696

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Abstract

Reaction of the lithium α-sulfinyl carbanion of chloromethyl phenyl sulfoxide with α, β-alkenyl carboxylic acid chlorides gave γ, δ-alkenyl α-chloro-β-keto sulfoxides in variable yields. The keto sulfoxides were also synthesized from α, β-alkenyl aldehydes in two steps in good overall yields: addition of the lithium α-sulfinyl carbanion of chloromethyl phenyl sulfoxide to α, β-alkenyl aldehydes followed by oxidation of the adducts with 2, 3-dichloro-5, 6-dicyano ...