Protodeboronation of tertiary boronic esters: Asymmetric synthesis of tertiary alkyl stereogenic centers

…, RP Sonawane, TG Elford, VK Aggarwal

Index: Nave, Stefan; Sonawane, Ravindra P.; Elford, Tim G.; Aggarwal, Varinder K. Journal of the American Chemical Society, 2010 , vol. 132, # 48 p. 17096 - 17098

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Citation Number: 97

Abstract

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 ...

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