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An efficient and convergent route towards water-soluble, chiral and amphiphilic macrocycles

✍ Scribed by Tapes Bhattacharyya; Ulf J Nilsson

Book ID
104230373
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
58 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A practical procedure for the synthesis of water-soluble, chiral and amphiphilic macrocyclic molecules is described. Acylation of p-xylylene diamine with Fmoc-protected glycine and aspartic acid, followed by removal of the Fmoc moiety afforded amino acid:p-xylene conjugates as free diamines. These diamines were converted to symmetrical and unsymmetrical macrocycles via stepwise urea formation using p-nitrophenyl chloroformate.

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In continuation of a work to develop water-soluble phosphanes for two-phase catalysis, nucleophilic phosphanylations of potassium or lithium salts of fluoroaromatic compounds are carried out. Ligands such as (III)-(VI) and (VIII) and (X) are characterized by NMR and mass spectroscopy. -(HINGST, M.;