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Updated: May 27, 2025

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Highly Stereoselective Synthesis of α-Oxoketene N,X-Acetals (X = O, S, or N) under Mild Conditions
Jia-Cheng Li1,2, Jia-Wang Li1,2, Rui Zhang1
1Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China.
Abstract:
A straightforward synthesis of α-oxoketene N,X-acetals (X = O, S, or N) from β-oxoamides has been described. The oxyphosphonium intermediates are quickly generated in situ from β-oxoamides in the presence of Hendrickson reagent and triflic anhydride (Tf2O) in a chemoselective manner and undergo a chemoselective nucleophilic substitution with phenols, thiophenols, or aromatic amines to deliver the desired products with high stereoselectivity. The one-pot synthetic protocol features readily available starting materials, mild conditions, simple execution, and a wide range of synthetic potentials of the products.
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