Highly Stereoselective Synthesis of α-Oxoketene N,X-Acetals (X = O, S, or N) under Mild Conditions

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-17 DOI:10.1021/acs.orglett.5c00174

Jia-Cheng Li, Jia-Wang Li, Rui Zhang, Dewen Dong

引用次数: 0

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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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.