Defining Aldol Chemoselectivity in the Presence of Henry Nucleophiles (Nitroalkanes).

ABSTRACT: This study evaluates the feasibility of achieving chemoselective aldol reactions over competing Henry reactions and employs competition experiments to establish proof of concept. A typical reaction involved using in-water reaction conditions where a concentrated organic layer containing an aldol nucleophile (1.5 equiv), a Henry nucleophile (1.5 equiv), an aldehyde electrophile (1.0 equiv), and a proline-based amino acid catalyst (2.5 mol%) constituted one phase, while the second phase was water (15 equiv). Highly enantioenriched aldol products were formed in practical yields, and a variety of Henry nucleophiles (nitroalkanes, allylic nitro compounds, and ethyl nitroacetate) were tolerated. This systematic examination of nitro compounds (pK_a 5.5-10.0) established a pK_a

SUBMITTER: Dwivedi KB 

PROVIDER: S-EPMC12735628 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature