AI Article Synopsis
- Researchers discovered that triazolium precatalysts, in the presence of a base, can effectively drive selective crossed acyloin condensation reactions between different types of aldehydes.
- An o-bromine atom acts as a temporary directing group to enhance chemoselectivity, which can easily be removed afterward.
- The method is straightforward and applicable to a wide range of substrates, and early results suggest that it can be adapted to produce highly enantioselective outcomes using chiral precatalysts.
Article Abstract
It has been shown for the first time that triazolium precatalysts promote (in the presence of base) highly chemoselective crossed acyloin condensation reactions between aliphatic and ortho-substituted aromatic aldehydes. An o-bromine atom can serve as a temporary directing group to ensure high chemoselectivity (regardless of the nature of the other substituents on the aromatic ring) which then can be conveniently removed. The process is of broad scope and is operationally simple as it does not require the preactivation of any of the coupling partners to ensure selectivity. Preliminary data indicate that highly enantioselective variants of the reaction are feasible using chiral precatalysts.
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| http://dx.doi.org/10.1021/jo101791w | DOI Listing |
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