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2022•Organic LettersRequires access

Synthesis of Tetrahydro-2H-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

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Abstract

An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2 H -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.

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What this paper is about

An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2 H -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.

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Available abstract

An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2 H -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.

Key concepts: Synthon, Annulation, Thiopyran, Chemistry, Sulfone, Combinatorial chemistry, Stereochemistry, Organic chemistry

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Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon — Research Paper | ScholarLens