Efficient synthesis of α,β-dichlorinated ketones from α,β-dichlorinated Weinreb amides through a simple work-up procedure.

Org Biomol Chem

Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, N10W5 Sapporo 060-0810, Japan.

Published: September 2021

AI Article Synopsis

  • The text outlines a method for creating α,β-dichlorinated ketones from α,β-dichlorinated Weinreb amides.
  • By using nonaqueous HCl for quenching, this approach minimizes side reactions that usually occur during traditional work-up processes.
  • Additionally, the method allows the amide to react with different nucleophiles, yielding high amounts of the desired ketones and presenting a unique reactivity for the Weinreb amide.

Article Abstract

An efficient synthesis of α,β-dichlorinated ketones from α,β-dichlorinated Weinreb amides is described. Quenching with nonaqueous HCl avoided side reactions associated with typical work-up procedures. The amide reacted with various nucleophiles to give the corresponding ketones in high yields. A novel reactivity of the Weinreb amide is also discussed.

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http://dx.doi.org/10.1039/d1ob01379cDOI Listing

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