Stereoselective Substituted Oxasilinane Synthesis from Diallylsilanes via Electrophile-Promoted Rearrangement, RCM, and Re-Catalyzed Allylic Transposition
Gregory W. O’Neil, Inna A. Fomina, Christopher R. Myers, Zachary T. Rademacher, Rawley M. Spencer, Robert F. Berger · 2026
Read Stereoselective Substituted Oxasilinane Synthesis from Diallylsilanes via Electrophile-Promoted Rearrangement, RCM, and Re-Catalyzed Allylic Transposition by Gregory W. O’Neil, Inna A. Fomina, Christopher R. Myers, Zachary T. Rademacher, Rawley M. Spencer, Robert F. Berger (2026) in the Tower of Babel, a free online library of public-domain works preserved in clean, searchable text. No sign-up. The full text is served as a plain-text file at a predictable URL, where text is present: https://antarctic-labs.com/tower-of-babel/PMC13459414.txt.
Description
O'Neil and colleagues report a route to oxasilinanes, six membered rings holding silicon and oxygen, used as building blocks and as stand ins that shield alcohol groups. Their 2026 study starts from diallylsilanes. An iodine rearrangement and a ring closing step make an eight membered ring. A rhenium oxide catalyst shrinks that ring, sliding a double bond into a new position and setting its shape as it goes.
The slide step turned out to be reversible. Left longer, the reaction kept converting starting material. The product ratio drifted toward the more stable cis form, the arrangement with substituents on the same face. A test run reached partway in ten minutes but finished within ninety, giving the product in good yield. That reversibility is a lever: reaction time becomes a dial for choosing which shape dominates. The sequence widens the menu of such rings for natural product synthesis and materials work.
Catalog record
| CREATOR | Gregory W. O’Neil, Inna A. Fomina, Christopher R. Myers, Zachary T. Rademacher, Rawley M. Spencer, Robert F. Berger |
|---|---|
| YEAR | 2026 |
| COLLECTION | PAPERS |
| FORMAT | TXT |
| FILE SIZE | 37 KB |
| LICENSE | https://creativecommons.org/licenses/by/4.0 |
| RIGHTS | CC BY |
| SOURCE | Europe PMC |