Strong Base-Promoted Pd-Catalyzed Asymmetric Hydroalkoxylation of Alkoxyallene
Abstract
A new protocol for the Pd-catalyzed hydroalkoxylation of alkoxyallene is presented that proceeds under strongly basic conditions. Notably, this method accommodates sterically hindered tertiary alcohols and carbohydrate-derived alcohols, which proved unreactive under the previous base-free conditions. This result was rationalized by the outer-sphere addition of alkoxide nucleophile to the syn π–allyl complex. Synthetic utility of the reaction was demonstrated by convergent synthesis of [1,4]-linked pentasaccharide.
Fields of Study & Subjects
Catalytic Alkyne Reactions
Carbohydrate Chemistry and Synthesis
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 3
- Pages
- 966–970
- Publication date
- 12 January 2026
- Language
- EN