Catalytic asymmetric synthesis of pyrrolidine derivatives bearing heteroatom-substituted quaternary stereocenters

2018 ◽  
Vol 5 (1) ◽  
pp. 36-40 ◽  
Author(s):  
Zhi-Peng Wang ◽  
Qi Wu ◽  
Jia Jiang ◽  
Zi-Rui Li ◽  
Xiao-Jiao Peng ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

An enantioselective [3 + 2] cycloaddition of heteroatom-substituted alkenes with α-substituted isocyanoacetates has been developed. Excellent reactivity and enantioselectivity were obtained.

scholarly journals Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Tao-Tao Gao ◽  
Hou-Xiang Lu ◽  
Peng-Chao Gao ◽  
Bi-Jie Li
Keyword(s):  
Asymmetric Synthesis ◽  
Amide Group ◽  
Enantioselective Synthesis ◽  
Biologically Active ◽  
Catalytic Asymmetric Synthesis ◽  
Boronic Esters ◽  
Synthetic Intermediates ◽  
Michael Acceptors ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

AbstractChiral tertiary boronic esters are important precursors to bioactive compounds and versatile synthetic intermediates to molecules containing quaternary stereocenters. The development of conjugate boryl addition to α,β-unsaturated amide has been hampered by the intrinsic low electrophilicity of the amide group. Here we show the catalytic asymmetric synthesis of enantioenriched tertiary boronic esters through hydroboration of β,β-disubstituted α,β-unsaturated amides. The Rh-catalyzed hydroboration occurs with previously unattainable selectivity to provide tertiary boronic esters in high enantioselectivity. This strategy opens a door for the hydroboration of inert Michael acceptors with high stereocontrol and may provide future applications in the synthesis of biologically active molecules.

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