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Updated: Sep 13, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Cr-Catalyzed Cyclic Homoallylic 1,2-Diol Synthesis through Photoredox Direct Hydrogen Atom Transfer
Ying Li1, Qiang Hu1, Tianlong Zeng1
1College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, China.
Abstract:
The cyclic homoallylic 1,2-diol motif is commonly found in a wide range of natural products and biologically active compounds. Herein, we report an efficient method for constructing this structural motif via a chromium-catalyzed reaction between aldehydes and cyclic silyl enol ethers (32 examples, up to 82% yield). The key to this transformation is the dual role of benzophenone, which serves both as a hydrogen atom transfer (HAT) reagent and as a reductant in the chromium catalytic cycle. The reaction proceeds under mild conditions and exhibits broad functional group tolerance. Furthermore, the use of a bisoxazoline ligand enables good enantioselective control and affords synthetically useful yields.
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