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

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This is a Experimental Study study.

Kosuke Ono; Jun Fukumoto; Yu Tanoi; Hidetoshi Kawai

doi:10.1039/d5qo01179e

January 1, 2025Organic Chemistry Frontiers

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

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Key Points

The reaction shows enhanced diastereoselectivity when conducted in mixed solvents, improving yield and purity.
Results indicate that variations in alkyl chain lengths affect the regioselectivity of the macrocyclization process.
The use of specific co-solvents significantly impacts the efficiency and selectivity of the benzoin condensation reaction.
These findings highlight the intricate role of solvent interactions in guiding product formation in organic synthesis.

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Implication

Experimental observation demonstrates diastereoselective production of macrocycles in benzoin condensation, suggesting solvent choice significantly influences outcomes.

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,...

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Cite This Study

Ono et al. (2025) studied this question.

synapsesocial.com/papers/68e03501f0e39f13e7fa3847 https://doi.org/10.1039/d5qo01179e

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

Key Points

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Implication

Abstract

Discussion

Cite This Study

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

Key Points

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Implication

Abstract

Discussion

Cite This Study

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