Synthesis of Tetrahydro-2<i>H</i>-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon
Xiang‐Long Chen, Huai‐Yu Wang, Chun‐Yan Wu, Bo‐Cheng Tang, Yao-Luo Hu, Jin‐Tian Ma, Shi‐Yi Zhuang, Zhi‐Cheng Yu, Yan‐Dong Wu, An‐Xin Wu
Abstract
An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2H-thiopyran 1,1-dioxides. Notably, rongalite acted as a tethered C–S synthon in this reaction and can be chemoselectively used as triple C1 units and as a source of sulfone. Mechanistic investigation indicated that two different carbon-increasing models are involved in this reaction in which rongalite serves as C1 units.
Topics & Concepts
SynthonAnnulationThiopyranChemistrySulfoneCombinatorial chemistryStereochemistryOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesSynthesis of heterocyclic compoundsSynthesis and Catalytic Reactions