Pd-catalyzed asymmetric carbonyl alkynylation:Synthesis of axial chiral ynones

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外文摘要：Ynones are important skeletons in bioactive molecules and valuable building blocks for organic synthe-sis,thus great efforts have been devoted to their preparation.While,introducing prochiral substrates to construct ynones bearing a chiral framework is unrealized to date.Herein,we reported the first example of Pd/SOP-catalyzed asymmetric carbonylative alkynylation via a non-classical carbonylative Sonogashira-type approach(acyl-Pd(Ⅱ)species generated from nucleophiles).By using cyclic diaryliodonium salts as prochiral substrates,various axial chiral ynones with good functional group tolerance(39 examples),sat-isfied yields(71％-96％)and excellent enantioselectivities(generally 94％-99％ee)were produced.Synthesis of bioactive compounds,scale-up experiment and useful transformations were also conducted to demon-strate the utility of this process.

外文关键词：

Pd-catalyzedAxial chiral ynonesCyclic diaryliodoniumHigh-valent palladium catalyzedAsymmetric carbonyl alkynylation

作者：

Long Jin、Jian Han、Dongmei Fang、Min Wang、Jian Liao

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作者单位：

Natural Products Research Center,Chengdu Institute of Biology,Chinese Academy of Sciences,Chengdu 610041,China

University of Chinese Academy of Sciences,Beijing 100049,China

College of Chemical Engineering,Sichuan University,Chengdu 610065,China

基金：

National Nature Science Foundation of ChinaYouth Innovation Promotion Association CASBiological Resources Programme,Chinese Academy of SciencesSichuan Science and Technology Program

项目编号：

221712582022375KFJ-BRP-0082022ZYD0038

出版年：

2024

DOI：

10.1016/j.cclet.2023.109212

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(6)