The easily available adducts of sodium p-toluenesulfinate to both acrylonitrile or acrylic acid were efficiently transformed through a two-step, high-yielding sequence into ethyl 5-[(4- methylphenyl)sulfonyl]-3-oxopentanoate, a convenient source for the popular Nazarov’s reagent, ethyl 3-oxopent-4-enoate, which could be generated in situ by base-induced beta-elimination and used for annulation reactions.
Ethyl 5-[(4-Methylphenyl)sulfonyl]-3-Oxopentanoate: A Bench-Stable Synthon for Ethyl 3-Oxopent-4-enoate (Nazarov’s Reagent)
BENETTI, Simonetta;CARLI, Stefano;DE RISI, Carmela;POLLINI, Gian Piero;VERONESE, Augusto;ZANIRATO, Vinicio
2008
Abstract
The easily available adducts of sodium p-toluenesulfinate to both acrylonitrile or acrylic acid were efficiently transformed through a two-step, high-yielding sequence into ethyl 5-[(4- methylphenyl)sulfonyl]-3-oxopentanoate, a convenient source for the popular Nazarov’s reagent, ethyl 3-oxopent-4-enoate, which could be generated in situ by base-induced beta-elimination and used for annulation reactions.File in questo prodotto:
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