Template-Directed Quantitative One-Pot Synthesis of Homochiral Helical Receptors Enabling Enantioselective Binding

Kyung Mog Kim, Geunmoo Song, Seungwon Lee, Hae Geun Jeon, Woojeong Chae, Kyu Sung Jeong

Research output: Contribution to journalArticlepeer-review

Abstract

Template-directed synthesis and dynamic covalent chemistry were implemented to achieve quantitative one-pot syntheses of homochiral helical cavities inside aromatic foldamers. One-handed helical receptors P-1, M-1, P-2 and M-2 were assembled from their precursors in the presence of appropriate templates (d- and l-tartaric acid, and d- and l-sorbitol, respectively) via three sequential steps in one pot: imine-linked chain elongation, template-induced folding and [4+2] cycloaddition between helical turns. These helical receptors were proven to enantioselectively bind chiral guests used as the templates, and the differences between the association constants of enantiomeric guests were up to more than two orders of magnitude. The structures and binding modes of the receptors were fully characterized by single-crystal X-ray crystallography and 1H NMR spectroscopy.

Original languageEnglish
Pages (from-to)22475-22479
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number50
DOIs
Publication statusPublished - 2020 Dec 7

Bibliographical note

Funding Information:
This study was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (2018R1A2A1A05077048). The authors acknowledge the Pohang Accelerator Laboratory (PAL) for beamline use (2019‐3rd‐2D‐027, 2020‐1st‐2D‐007).

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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