Tetrahedrally Arranged Tetraamide Macrocycle: Synthesis and Properties of L-Tartaric acid-based Macrocyclic Tetraamide
β Scribed by Heung-Jin Choi; Mi-Ok Kwak; Jong-Mok Kim
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 627 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A first example of chiral tetraamide macrocycles 2 and 3 of whichfour amide oxygen ligand sites can converge inward molecular cavity upon complexation w"thalkali metal ion were synthesized from p-xylylenediarnine and 2,3-O-isopropylidene-L-tartaiyl chloride, 1 derivedfrom L-tartaric acid. 01997 Elsevier Science Ltd.
π SIMILAR VOLUMES
Chiral a,v-diesters react under high-pressure conditions (10 kbar) with a,v-diamines to give chiral cyclic tetraamides of C 2symmetry. The complexation properties of tetraamides towards alkali metal cations (Li ΓΎ , Na ΓΎ , K ΓΎ , Rb ΓΎ and Cs ΓΎ ) were estimated on the basis of ESI-MS spectra.
The synthesis of new 16-, 18-, 19-or 20-membered secondary tetralactams with L-tartaric acid or 13-hydroxyglutaric acid moieties is investigated. The stepwise synthesis with an intermediate diamide diamine provides overall good yields (30-55%) compared with other processes using an intermediate diam