Regioselective Aryne Annulations of N-Tosyl-2-enamides and N-tert-Butylsulfinyl-2-enamides for the Construction of Dihydroquinolin-4-one and Chroman-4-imine Units

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-14 DOI:10.1021/acs.orglett.4c04571

Aimin Zhang, Suh Young Yu, Jihye Lee, Sehui Yang, Junseong Lee, Jimin Kim

引用次数: 0

Abstract

A regioselective synthesis of the dihydroquinolin-4-one 4 is achieved from the aryne-mediated annulation of an o-(trimethylsilyl)aryl triflate 1 with N-tosyl-2-enamide 2 in the presence of TBAT in toluene, whereas the chroman-4-imine 5 is formed from the reaction of 1 with N-(tert-butylsulfinyl)-2-enamide 3 and TBAF in THF. Governing factors for regioselectivity have been accounted for as strong steric and electronic effects between N-toluenesulfonyl and N-tert-butylsulfinyl groups in 2 and 3. The methods described herein are successful with various substrates 1 with 2 or 3 in high levels of regioselectivity, and diastereoselectivity for 5.

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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.