Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters

A palladium-catalyzed enantioselective decarboxylative allylic alkylation of alpha-benzyl cyanoacetates with methylene cyclic carbamates has been successfully developed. An array of enantioenriched products bearing nitrile-containing acyclic quaternary carbon stereocenters were obtained in high yiel...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 23; pp. 5971 - 5977
Main Authors Bao, Qing, Sun, Ting-Jia, Zhang, Yan-Ping, Wang, Zhen-Hua, You, Yong, Ge, Zhen-Zhen, Zhou, Ming-Qiang, Zhao, Jian-Qiang, Yuan, Wei-Cheng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.11.2023
Royal Society of Chemistry
Subjects
Alkylation
Carbamates (tradename)
Carbon
Chemistry
Chemistry, Organic
Enantiomers
Organic chemistry
Palladium
Physical Sciences
Science & Technology
SUBSTITUTION
REAGENTS
ASYMMETRIC CONJUGATE ADDITION
LIGANDS
ADJACENT QUATERNARY
NATURAL-PRODUCTS
CONSTRUCTION
ALLYLATION
STEREOGENIC CENTERS
TERTIARY
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Summary:A palladium-catalyzed enantioselective decarboxylative allylic alkylation of alpha-benzyl cyanoacetates with methylene cyclic carbamates has been successfully developed. An array of enantioenriched products bearing nitrile-containing acyclic quaternary carbon stereocenters were obtained in high yields with good enantioselectivities (up to 99% yield and 93% ee). This method provides a new tactic for the construction of chiral nitrile-containing acyclic quaternary carbon stereocenters. A palladium-catalyzed enantioselective decarboxylative allylic alkylation of alpha-benzyl cyanoacetates with methylene cyclic carbamates was developed for the construction of nitrile-containing acyclic quaternary carbon stereocenters with good results.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d3qo01605f