Chiral Bronsted acid-catalysed enantioselective allylboration of sterically hindered aldehydes enabled by multiple hydrogen bonding interactions.

ABSTRACT: Chiral phosphoric acids (CPAs) are an important class of chiral Brønsted acid catalysts that can accomplish highly effective enantioselective allylborations of aldehydes. However, traditional CPA-catalysed allyboration has difficulty utilizing sterically hindered aldehydes, where the corresponding products of enantioenriched secondary alcohols adjacent to a quaternary carbon are important moieties in biologically active natural products. To overcome this issue, we employed a chiral phosphoramide catalyst for allylation and crotylation reactions of the allyl boronic acid pinacol ester with sterically hindered aldehydes to benefit from multiple hydrogen bonding interactions between the chiral phosphoramide and substrates. As a result, not only the sterically hindered aldehydes, but the less

SUBMITTER: Umemiya S 

PROVIDER: S-EPMC11817098 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature