Enantioselective access to chiral phosphonothioates via iridium-catalyzed asymmetric allylic substitution
Huailan Yang1, Zeng-Hua Wu1, Guang-Yao Ma1
1School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, China, 710119.
Abstract:
We report an efficient iridium-catalyzed asymmetric allylic substitution (AAS) protocol that enables the construction of branched allylic phosphonothioate derivatives under mild conditions. This catalytic system exhibits remarkable functional group compatibility across a structurally diverse range of substrates, delivering products with unprecedented stereocontrol (up to >99% ee) and excellent regioselectivity. By employing readily derivatizable phosphonothioic acid esters as nucleophiles, this method provides a versatile platform for accessing chiral organophosphorus scaffolds.
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Regioselectivity of Electrophilic Additions-Peroxide Effect
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Radical Anti-Markovnikov Addition to Alkenes: Overview
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration


