Asymmetric Synthesis of Tertiary Stereogenic Centers

Significance

Boronic esters represent a versatile class of synthetic intermediates in organic synthesis since they can be easily prepared in an enantio-selective fashion. Their transformation into other functional groups like alcohols and amines or their use in C-C coupling reactions under retention of configuration is well known. Herein, the authors present an efficient protocol for the protodeboronation of tertiary diarylalkyl and aryldialkyl boronic esters of type 2 into the corresponding products 3 with full retention of configuration and excellent yields. Furthermore, the applicability of this methodology has been proved in a short total synthesis of the small natural product (S)-­turmerone.