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Synfacts 2025; 21(10): 995
DOI: 10.1055/a-2680-8412
Synthesis of Materials and Unnatural Products

Preservable Chirality in Carbocation-Mediated Spiroannulation

Authors

    Contributor(s):

  • Dahui Zhao

  • Xinhang Chang

Pu X, Lu Y, Zhou Z, Yang Y, Zhang C, Yu P *, Zhao YS *, Lan J *, You J *. Southern University of Science and Technology, Shenzhen, Institute of Chemistry, Chinese Academy of Sciences, Beijing, and Sichuan University, Chengdu, P. R. China
Chirality Retention in Friedel–Crafts Spiroannulation for Iterative Synthesis of Spiro-Bridged Conjugated Carbocycles.

Nat. Synth. 2025;
DOI: 10.1038/s44160-025-00817-4
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Keywords

Friedel–Crafts alkylation - axially chiral carbocation - stereochemistry retention - C–H activation–annulation

Significance

An impressive stereo-retention process is observed with a Friedel–Crafts alkylation by virtue of the chirality memory of the transient, axially chiral spiro-carbocation intermediate, which allows the construction of enantiopure oligocarbocycles having chiral spirocenters.


 

Comment

Prior to the final step of intramolecular Friedel–Crafts spiro-annulation of multiple carbocycles, an iterative synthetic sequence involving repeated rhodium-catalyzed regioselective C–H activation–annulation is the key to realizing the chiral tertiary alcohol precursors.


 

 

Publication History

Article published online:
23 September 2025

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