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Updated: Jun 27, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

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尼-催化二元立体融合分子内基-基降解合:一条通往syn-Chromanols的路线

Sudipta Ghosh1, Arnab Rooj1, Rajesh Chakrabortty1

  • 1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, West Bengal, India.

Organic letters
|April 26, 2024
PubMed
概括

研究人员开发了一种新的催化反应,用于从化合物和化物中合成合成合成染色醇. 这种方法具有很高的选择性,适用于各种基质,使复杂分子的有效合成成为可能.

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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