scholarly journals Stereochemical Control of Enzymatic Carbon-Carbon Bond-Forming Michael-Type Additions by “Substrate Engineering”

2016 ◽  
Vol 2016 (32) ◽  
pp. 5350-5354 ◽  
Author(s):  
Yufeng Miao ◽  
Pieter G. Tepper ◽  
Edzard M. Geertsema ◽  
Gerrit J. Poelarends
Keyword(s):  
Carbon Bond ◽  
Bond Forming ◽  
Stereochemical Control ◽  
Carbon Carbon Bond ◽  
Substrate Engineering

Nickel-Catalyzed Electronically-Reversed Enantioselective Hydrocarbofunctionalizations of Acrylamides

Synlett ◽  
2021 ◽  
Author(s):  
Lou Shi ◽  
Wei Shu
Keyword(s):  
Nickel Catalyst ◽  
Functional Group ◽  
Optically Active ◽  
Forming Process ◽  
Carbon Bond ◽  
Bond Forming ◽  
Synthetic Strategy ◽  
Carbon Carbon Bond ◽  
Wide Range ◽  
Simple Protocol

Asymmetric hydrocarbofunctionalizations of alkenes has emerged as an efficient synthetic strategy for accessing optically active molecules via carbon-carbon bond-forming process from readily available alkenes and carbo-electrophiles. Herein, we present a summary of the efforts from our group to control the regio- and enantioselectivity of hydrocarbofunctionalizations of electron-deficient alkenes with a nickel catalyst and chiral bisoxazolidine ligand. The reaction undergoes electron-reversed hydrocarbofunctionalizations acrylamides with excellent enantioselectivity. This operationally simple protocol enables the asymmetric hydroalkylation, hydrobenzylation and hydropropargylation of acrylamides. This reaction is useful for preparing a wide range of α-branched chiral amides with broad functional group tolerance.

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