Regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones: asymmetric construction of N-containing quaternary stereocenters

The direct regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates alpha-hydrazido-alpha-alkynyl ketone products with high enantioselectivity. Control experiments indicate that...

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Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 19; pp. 5377 - 5382
Main Authors He, Faqian, Wang, Jiawen, Zhou, Fang, Tao, Houchao, Yang, Xiaoyu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.10.2021
Royal Society of Chemistry
Subjects
Amination
Amines
Asymmetric synthesis
Asymmetry
Catalysis
Chemistry
Chemistry, Organic
Enantiomers
Functional groups
Ketones
Organic chemistry
Phosphoric acid
Physical Sciences
Science & Technology
Stereoselectivity
Substrates
BRONSTED ACID
CATALYSIS
ELECTROPHILIC AMINATION
ALDEHYDES
CYANOACETATES
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Summary:The direct regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones with azodicarboxylates has been developed through chiral phosphoric acid catalysis, which generates alpha-hydrazido-alpha-alkynyl ketone products with high enantioselectivity. Control experiments indicate that the alpha-alkynyl group in the ketone substrate is critical for both the reactivity and stereoselectivity of the reaction. Facile derivatizations of the functional group-abundant chiral product further highlight the value of this approach in the asymmetric synthesis of alpha-tertiary amines and N-containing heterocycles.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo00720c