Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes

Abstract

A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. The reaction was also successfully implemented on a flow micro reactor system.

Keywords

• DFT
• diastereoselective reaction
• domino aldol
• metal enolate
• tetrahydropyran