Enantioselective Synthesis of Hydrindanes via Palladium-Catalyzed Asymmetric Desymmetrization of Cyclohexadiene Derivatives

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-05 DOI:10.1021/acs.orglett.4c04733

Shu Wu, Miaomiao Li, Jiajun Lu, Chi Yang, Yue Huang, Aijun Lin

引用次数: 0

Abstract

We herein disclose a strategy for the asymmetric desymmetrization of cyclohexadiene derivatives via a palladium-catalyzed Heck and tandem Heck/Tsuji-Trost allylic alkoxylation reaction. By employing DCE as the solvent, we obtained a variety of chiral hydrindanes containing an all-carbon quaternary carbon center and a tertiary carbon chiral center in good yields with excellent enantioselectivities. With alcohols as the solvent, the valuable chiral hydrindanes with one quaternary stereocenter and two tertiary centers were constructed with a high level of enantioinduction.

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钯催化环己二烯衍生物不对称脱对称对映选择性合成苯乙烯

本文通过钯催化Heck和串联Heck/Tsuji-Trost烯丙基烷氧基化反应，揭示了环己二烯衍生物的不对称去对称化策略。以DCE为溶剂，得到了多种含全碳型季碳中心和叔碳型手性中心的手性苯胺，产率高，对映选择性好。以醇为溶剂，以高水平的对映诱导作用合成了具有1个季位中心和2个叔位中心的有价手性苯烃。

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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.