Catalytic Asymmetric Vinylogous and Bisvinylogous Propargylic Substitution

Distinct regio- and enantioselectivity control in copper-catalyzed vinylogous and bisvinylogous propargylic substitution has been accomplished by using a novel chiral N,N,P ligand. The developed method provides an efficient and selective approach to an array of highly enantioenriched alkynyl unsatur...

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Published inJournal of the American Chemical Society Vol. 144; no. 34; pp. 15779 - 15785
Main Authors Qian, Hao-Dong, Li, Zhi-Heng, Deng, Shuang, Yao, Chaochao, Xiang, Hua-Ming, Xu, Guang, Geng, Zi-Qi, Wang, Zihao, Chen, Linfeng, Liu, Chunrong, Zhu, Cuiju, Qi, Xiaotian, Xu, Hao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.08.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
enantioselective synthesis
enantioselectivity
ligands
Physical Sciences
Science & Technology
ALDOL
CYCLOADDITION
AMINATION
COPPER
ENANTIOSELECTIVE ALLYLIC SUBSTITUTION
ESTERS
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Summary:Distinct regio- and enantioselectivity control in copper-catalyzed vinylogous and bisvinylogous propargylic substitution has been accomplished by using a novel chiral N,N,P ligand. The developed method provides an efficient and selective approach to an array of highly enantioenriched alkynyl unsaturated carbonyl compounds. Salient features include excellent functional group tolerance and broad substrate scope. The synthetic utility of the developed method is further demonstrated by a gram-scale synthesis and by application to a range of transformations including enantioselective synthesis of unique challenging compounds.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.2c06560