1201898-75-0Relevant academic research and scientific papers
Full chirality transfer in the conversion of secondary alcohols into tertiary boronic esters and alcohols using lithiation-borylation reactions
Bagutski, Viktor,French, Rosalind M.,Aggarwal, Varinder K.
supporting information; experimental part, p. 5142 - 5145 (2010/10/20)
New conditions, full transfer: Using MgBr2/MeOH as an additive now provides essentially 100 % retention of configuration in the lithiation-borylation reaction, thus leading to tertiary boronic esters (or tertiary alcohols) with exceptionally hi
Protodeboronation of tertiary boronic esters: Asymmetric synthesis of tertiary alkyl stereogenic centers
Nave, Stefan,Sonawane, Ravindra P.,Elford, Tim G.,Aggarwal, Varinder K.
, p. 17096 - 17098 (2011/03/01)
While tertiary boranes undergo efficient protodeboronation with carboxylic acids, tertiary boronic esters do not. Instead, we have discovered that CsF with 1.1 equiv of H2O (on tertiary diarylalkyl boronic esters) or TBAF?3H2O (on tertiary aryldialkyl boronic esters) effect highly efficient protodeboronation of tertiary boronic esters with essentially complete retention of configuration. Furthermore, substituting D2O for H2O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. The methodology has been applied to a short synthesis of the sesquiterpene, (S)-turmerone.
Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates
Bagutski, Viktor,Ros, Abel,Aggarwal, Varinder K.
supporting information; experimental part, p. 9956 - 9960 (2010/02/27)
A general method for the preparation of virtually any potassium trifluoroborate salt from the corresponding pinacolboronic ester is reported. Thus, conditions for an azeotropic removal of pinacol from the reaction mixture were found to afford the desired potassium trifluoroborates of sufficient purity (>95%) in nearly quantitative yields irrespective of the nature of the product. The utility of this method is illustrated by the preparation of a broad range of enantioenriched secondary and tertiary potassium trifluoroborates.
