Chemo- and Regioselectivity in Allenamide-Homoenolate Coupling

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-10 DOI:10.1021/acs.orglett.5c00124

Raju Teegala, Purna C. R. Bhavnari, Kadiyala Sagar, Arun B. Ingle, Tapas R. Pradhan, Jin Kyoon Park

引用次数: 0

Abstract

We report herein a chelation assisted, ring-strain-driven homoenolate interception with allenamides, proceeding through a complementary reactivity pattern─noncycloaddition and central C interception of C-pronucleophiles─distinct from previous studies. The developed atom-economical method provides access to carbonyl-tagged enamides with high chemo- and regioselectivity, offering a broad scope and significant synthetic value, as demonstrated by further diversification. The origin of the selectivity is clarified through experimental mechanistic investigations, revealing the detailed reaction pathway proceeding through a carbopalladation event.

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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.