Abstract
A “green” and practical intramolecular pinacol coupling reaction promoted by InCl3/Al catalysts in aqueous media has been developed. Under mild conditions, a novel class of polysubstituted cyclopentane-1,2-diols have been obtained with excellent diastereoselectivity.
Highlights
In organic synthesis, the formation of carbon-carbon bonds is one of the most fundamental and important operations in the construction of functional molecules
Since its discovery in 1859 [2], the pinacol coupling reaction has been a focal point in synthetic chemistry for its carbon-carbon bond generating power, and for the wide utility of the 1,2-diols obtained from these reactions
In our previous work studying indium catalysis, we developed InCl3/Al catalyzed pinacol coupling reactions in aqueous media, in which a class of vicinal diols derived from aromatic aldehydes, ketones and aldehyde-ketone cross coupling have been synthesized in good yields [22]
Summary
The formation of carbon-carbon bonds is one of the most fundamental and important operations in the construction of functional molecules. Unlike the corresponding intermolecular reactions, intramolecular pinacol coupling reactions furnish cyclized diols, which usually limits their applications
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