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Synfacts 2025; 21(01): 74
DOI: 10.1055/a-2467-5022
Organo- and Biocatalysis

Catalytic Asymmetric Cracking of Cyclopropanes

Contributor(s):
Benjamin List 
,
Fuxing Shi
Raut RK, Matsutani S, Shi F, Katakoa S, Poje M, Mitschke B, Maeda S, Tsuji N *, List B *. Hokkaido University, Sapporo, Japan and Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Catalytic Asymmetric Fragmentation of Cyclopropanes.

Science 2024;
386: 225-230
DOI: 10.1126/science.adp9061
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Keywords

alkane activation - cyclopropanes - organocatalyst - asymmetric catalysis - cycloproponium ions - catalytic cracking

Significance

The List group develops a highly enantioselective fragmentation of cyclopropanes using chiral Brønsted acid catalysis with well-defined active sites. A series of saturated cyclopropanes were protonated to afford the corresponding alkenes with excellent enantioselectivities. The approach delineated in this study pushes the boundary of organocatalytic alkane activation achieved by artificial molecules (catalyst) and could further expand the utilization of Brønsted acid catalysis in hydrocarbon chemistry.


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Comment

Until today, the catalytic and stereoselective activation of alkanes has been one of the most challenging tasks in chemistry, with no general stereoselective activation of saturated and further unactivated cyclopropanes achieved. This work demonstrates the enantioselective fragmentation of fully saturated cyclopropanes using IDPi Brønsted acid catalysis. This process could be regarded as asymmetric “cracking” of cyclopropanes, similar to petroleum chemistry.


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Publication History

Article published online:
20 December 2024

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