Highly Enantioselective Synthesis of Phosphorus‐Containing ϵ‐Benzosultams by Bifunctional Phosphonium Salt‐Promoted Hydrophosphonylation
Song Zhang, Zhenghuai Feng, Chunhui Jiang, Xiaojun Yu, Jianke Pan, Juan Du, Zhiyu Jiang, Yuan Chen, Tianli Wang
Abstract
ϵ-Benzosultam derivatives are potential drug candidates with diverse biological activities. A series of chiral ϵ-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished. Some control experiments were also conducted to elucidate the plausible reaction mechanism of this chemical transformation.
Topics & Concepts
BifunctionalPhosphonium saltPhosphoniumEnantioselective synthesisSalt (chemistry)CatalysisChemistryPhosphorusOrganic chemistryCombinatorial chemistryOrganophosphorus compounds synthesisAsymmetric Hydrogenation and CatalysisSynthesis and Reactivity of Sulfur-Containing Compounds