Enantioselective synthesis of α-phenyl- and α-(dimethylphenylsilyl)alkylboronic esters by ligand mediated stereoinductive reagent-controlled homologation using configurationally labile carbenoids

2015 ◽  
Vol 13 (12) ◽  
pp. 3781-3786 ◽  
Author(s):  
Adam L. Barsamian ◽  
Zhenhua Wu ◽  
Paul R. Blakemore
Keyword(s):  
Enantioselective Synthesis ◽  
Chain Extension ◽  
Boronic Esters

Enantioselective chain extension of boronic esters with configurationally labile racemic carbenoids is achieved in the presence of scalemic bisoxazoline ligands.

ChemInform Abstract: Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation-Borylation of Propargylic Carbamates.

ChemInform ◽  
2013 ◽  
Vol 44 (15) ◽  
pp. no-no
Author(s):  
Benjamin M. Partridge ◽  
Laetitia Chausset-Boissarie ◽  
Matthew Burns ◽  
Alexander P. Pulis ◽  
Varinder K. Aggarwal
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Boronic Esters

Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation-Borylation of Propargylic Carbamates

2012 ◽  
Vol 51 (47) ◽  
pp. 11795-11799 ◽  
Author(s):  
Benjamin M. Partridge ◽  
Laëtitia Chausset-Boissarie ◽  
Matthew Burns ◽  
Alexander P. Pulis ◽  
Varinder K. Aggarwal
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Boronic Esters

Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation-Borylation of Propargylic Carbamates

2012 ◽  
Vol 124 (47) ◽  
pp. 11965-11969 ◽  
Author(s):  
Benjamin M. Partridge ◽  
Laëtitia Chausset-Boissarie ◽  
Matthew Burns ◽  
Alexander P. Pulis ◽  
Varinder K. Aggarwal
Keyword(s):  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Boronic Esters

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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