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SYNTHETIC METHODOLOGY

The gains from breaking symmetry

Nature Chemistry volume 13, pages 623–624 (2021)Cite this article

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All-carbon quaternary centres are challenging targets in organic synthesis. Now, the development of a zinc-catalysed desymmetrization method enables the synthesis of chiral alcohols with all-carbon quaternary centres by the selective reduction of symmetrical α,α-disubstituted malonates.

Although it is said that nature is an inexhaustible source of chiral products, compounds are usually formed as a single enantiomer, leaving the problem of acquiring the opposite enantiomer. Throughout the years there has been a shift from methods using raw materials of natural origin to synthetic approaches using either stoichiometric (less frequent approach) or catalytic (currently dominant approach) amounts of chirality inducers — either chiral auxiliaries or catalysts1. Chiral catalysts used in asymmetric synthesis should be highly active, readily available, and cost-effective, but meeting all of these requirements in a single system is rarely observed.

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Fig. 1: Zinc-catalysed desymmetrization reaction of malonic esters.

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  1. Department of Chemistry, Adam Mickiewicz University, Poznań, Poland

    Jadwiga Gajewy & Marcin Kwit

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  1. Jadwiga Gajewy
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  2. Marcin Kwit
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Correspondence to Marcin Kwit.

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The authors declare no competing interests.

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Gajewy, J., Kwit, M. The gains from breaking symmetry. Nat. Chem. 13, 623–624 (2021). https://doi.org/10.1038/s41557-021-00731-0

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