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
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.
