DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-20 DOI:10.1021/acs.orglett.4c03842

Dongqiu Li, Jiale Wu, LuLu Yang, Shuangshuang Cai, Yuhai Tang, Yang Li, Silong Xu

引用次数: 0

Abstract

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, and E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates 1 use the β- and ε-carbons for the bond formation, presenting new and regiodivergent C₄ synthons for Lewis base-catalyzed annulations.

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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.