Catalytic Asymmetric Cycloaddition of Olefins with In Situ Generated <i>N</i>-Boc-Formaldimine.

ABSTRACT: Chiral 1,3-amino alcohols are ubiquitous structural motifs in natural products and active pharmaceutical ingredients. We present a highly enantioselective, inverse-electron-demand hetero-Diels-Alder reaction of olefins with in situ generated N-Boc-formaldimine catalyzed by strong and confined Bro̷nsted acids. This transformation provides direct access to valuable 1,3-amino alcohols from styrenes and 1,1-disubtituted alkenes. Isotope labeling studies and kinetic analysis reveal an unusual mechanism involving an oxazinium intermediate and a catalyst order greater than one.

SUBMITTER: Guillen M 

PROVIDER: S-EPMC11613496 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature