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Organic chemistry

Catalysis in tight spaces

Nature volume 483, pages 278–279 (2012)Cite this article

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An acid has been found to catalyse the formation of a common chemical group, the spiroacetals, and to control which mirror-image isomer of the group is made. The key to success is the acid's bulky molecular structure. See Letter p.315

Opposites attract. When applied to the charges in organic molecules, this idea serves as a foundation for understanding how such molecules react. A large portion of organic chemistry can be explained by the concept that electron-rich molecules (or sites on molecules), which have negative character, seek to interact with, and potentially donate electrons to, electron-poor species that have positive character. On page 315 of this issue, Čorić and List1 describe a fresh use of this concept, with a report of a negatively charged, bulky catalyst that controls the reaction of a positively charged intermediate in the synthesis of potentially useful compounds known as spiroacetals.

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Figure 1: Acetals and an acetal precursor.
Figure 2: A spiroacetal-forming reaction.

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Authors and Affiliations

  1. Noah Z. Burns and Eric N. Jacobsen are in the Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.,

    Noah Z. Burns & Eric N. Jacobsen

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  1. Noah Z. Burns
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  2. Eric N. Jacobsen
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Correspondence to Eric N. Jacobsen.

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Burns, N., Jacobsen, E. Catalysis in tight spaces. Nature 483, 278–279 (2012). https://doi.org/10.1038/483278a

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