Enantioselective Synthesis of Quaternary Stereocenters via a Catalytic Asymmetric Stetter Reaction

2004 ◽  
Vol 126 (29) ◽  
pp. 8876-8877 ◽  
Author(s):  
Mark S. Kerr ◽  
Tomislav Rovis
Keyword(s):  
Enantioselective Synthesis ◽  
Stetter Reaction ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

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.

scholarly journals Enantioselective synthesis of (−)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction

2016 ◽  
Vol 14 (1) ◽  
pp. 93-96 ◽  
Author(s):  
Allegra Franchino ◽  
Pavol Jakubec ◽  
Darren J. Dixon
Keyword(s):  
Aldol Reaction ◽  
Enantioselective Synthesis ◽  
Asymmetric Aldol ◽  
Asymmetric Aldol Reaction ◽  
Catalytic Asymmetric

A concise synthesis of (−)-chloramphenicol, based on the catalytic asymmetric aldol reaction between 4-nitrobenzaldehyde and benzhydryl isocyanoacetate, is reported.

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