Phosphine-Catalyzed anti-Carboboration of Alkynoates with 9-BBN-Based 1,1-Diborylalkanes: Synthesis and Use of Multisubstituted γ-Borylallylboranes.
Ayaka YamazakiKazunori NagaoTomohiro IwaiHirohisa OhmiyaMasaya SawamuraPublished in: Angewandte Chemie (International ed. in English) (2018)
Trialkylphosphine organocatalysis has enabled the regioselective anti-carboboration of alkynoates with 9-BBN-based 1,1-diborylalkanes to produce secondary allylboranes with β-alkoxycarbonyl and γ-boryl substituents. The utility of the densely functionalized allylboranes was demonstrated by the highly diastereoselective allylation of N-(trimethylsilyl)aldimines to produce homoallylamines containing tertiary allylborane and acrylate moieties.