Catalytic methods for the generation of chiral bis(boronates): The utility of saturated carbon -boron bonds.

摘要

Described herein is working involving new catalytic processes which allow access to reactive bis(boronate) intermediates. A rhodium-QUINAP catalyst is developed for the asymmetric diboration of simple alkenes. Functionalization of the 1,2-alkyl bis(boronate) intermediates leads to the 1,2-diol, 1,4-diol, and 1,2-carbohydroxylation products. Catalytic asymmetric hydrogenation with a rhodium-Walphos complex is also utilized as a method for the synthesis of 1,2-alkyl bis(boronates). A platinum-catalyzed 1,3-diene diboration/asymmetric aldehyde allylation is also developed for the synthesis of 1,3-diols containing an all-carbon quaternary stereocenter.