Racemization of Cross-Chain Bridging Cryptands: Effects of Linker Combination on Racemization Rate

We synthesized three 28-membered chiral cross-chain bridging cryptands ([3.3.6], [4.4.5], and [5.5.4]) with three different linker combinations. After the separation of their enantiomers, the racemization behavior of the cryptands was evaluated by chiral high-performance liquid chromatography. As the number of ethylene glycol units in the two cross-chain linkages increased, the racemization reaction proceeded slowly.

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Publication Details

Journal
Organic Letters
Published
2025-05-06
DOI
https://doi.org/10.1021/acs.orglett.5c01161
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Racemization of Cross-Chain Bridging Cryptands: Effects of Linker Combination on Racemization Rate

Shinobu Miyagawa, Takashi Maruyama, Yuji Tokunaga, S Niimi
Organic Letters
Chemical Synthesis and Analysis
article

Racemization of Cross-Chain Bridging Cryptands: Effects of Linker Combination on Racemization Rate

Shinobu Miyagawa, Takashi Maruyama, Yuji Tokunaga, S Niimi
article en

Abstract

We synthesized three 28-membered chiral cross-chain bridging cryptands ([3.3.6], [4.4.5], and [5.5.4]) with three different linker combinations. After the separation of their enantiomers, the racemization behavior of the cryptands was evaluated by chiral high-performance liquid chromatography. As the number of ethylene glycol units in the two cross-chain linkages increased, the racemization reaction proceeded slowly.

Organic LettersVol. 27(19)
University of Fukui (JP)
Japan Society for the Promotion of Science
Zero hunger
Openalex Percentile: Top 91%
Chemical Synthesis and Analysis
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