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Updated: Jul 8, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Hydroxyl-Directed Regio- and Diastereoselective Allylic Sulfone Reductions with [Sm(H2O)]I2
Cody L Schwans1, Trevor D Clark1, Gregory W O'Neil1
1Department of Chemistry, Western Washington University, Bellingham, Washington 98225, United States.
Abstract:
Allylic 1,2- and 1,3-hydroxy phenyl sulfones undergo regioselective and diastereoselective desulfonylation with double bond migration upon treatment with [Sm(H2O)]I2. Selectivity in these reactions is thought to arise from the formation of a chelated organosamarium intermediate followed by intramolecular protonation by samarium-bound water, which is supported by observed diastereoselectivity and stereospecificity trends along with deuterium labeling experiments. The reaction was then featured in the synthesis of the phenolic fragment of the thailandamide natural products.
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