Precipitation-Driven Diastereo- and Regioselective Macrocyclization via Benzoin Condensation: Effects of Solvents and Alkyl Chain Lengths

Abstract

The benzoin condensation of a designed dialdehyde 1 with a terphenyl framework was investigated. When the reaction was carried out in mixed solvents composed of an alcohol and a co-solvent, a precipitate primarily consisting of the cyclic dimer meso-2 was obtained, indicating a precipitation-driven diastereo- and regioselective self-assembly process. Using this system as a model for precipitation-induced self-assembly based on reversible C-C bond formation, we comprehensively investigated the effects of the alcohol, co-solvent, and alkyl chain length of the substrate on the outcome of the reaction. Notably, the reaction of ethoxy-substituted dialdehyde 1 in MeOH/toluene mixture reached equilibrium efficiently, affording a crystalline precipitate incorporating macrocycle meso-2 and toluene, from which meso-2 was isolated in good yield.

Supplementary files

Article information

Article type
Research Article
Submitted
15 Aug 2025
Accepted
01 Oct 2025
First published
03 Oct 2025

Org. Chem. Front., 2025, Accepted Manuscript

Precipitation-Driven Diastereo- and Regioselective Macrocyclization via Benzoin Condensation: Effects of Solvents and Alkyl Chain Lengths

K. Ono, J. Fukumoto, Y. Tanoi and H. Kawai, Org. Chem. Front., 2025, Accepted Manuscript , DOI: 10.1039/D5QO01179E

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