Synthesis of Diastereo- and Enantioenriched Homoallylic Alcohols with a Chiral CF₃- and F-Bound Carbon

Key words

zinc catalysis - pyranosides - catalyst control

Significance

Hoveyda and coworkers report a regio-, diastereo- and enantioselective reaction between polyfluoro allylboronates and aldehydes. ­Diastereomeric polyfluoro monosaccharides were accessible from the homoallylic alcohols generated from the authors’ catalyst-controlled methodology, and a known substrate-controlled route.

Comment

The CF₃ and F substituents are important for the γ-selectivity, as α-selectivity resulting from direct allyl addition is observed when the F is replaced with an H atom. These substituents are also responsible for unusual preferential benzylation at the 2° over 1° alcohol, in one of the intermediates leading to the final pyranoside.

Publication History

Article published online:
17 January 2023