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Nitrogen-containing macrocycles having a carbohydrate scaffold.
Adv Carbohydr Chem Biochem
November 2024
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. Electronic address:
Article Synopsis
- Nitrogen-containing macrocyclic compounds like amines and amides are key focuses in supramolecular chemistry, particularly aza-macrocycles that include sugar units.
- The article categorizes various types of carbohydrate-based macrocycles, including aza-crown ethers, cyclic oligomers from amino sugars, and nitrogen-containing glycophanes.
- It also reviews strategies for creating these compounds and highlights their applications as important receptors in supramolecular chemistry.
Synthesis of d-mannitol-based crown ethers and their application as catalyst in asymmetric phase transfer reactions.
Chirality
April 2018
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary.
A few new d-mannitol-based monoaza-15-crown-5 type chiral lariat ethers and 18-crown-6 type macrocycles were synthesized. These crown compounds were used as phase transfer catalysts in asymmetric Michael addititons and in a Darzens condensation under mild conditions to afford the corresponding products in a few cases in good to excellent enantioselectivities. In the Michael addition of diethyl acetoxymalonate to trans-chalcone, in the addition of diethyl acetamidomalonate to ß-nitrostyrene, in the reaction of diethyl bromomalonate with benzylidene malononitriles, in the cyclopropanation reaction of diethyl bromomalonate and 2-benzylidene-1,3-indandione, and in the Darzens condensation of α-chloroacetophenone with benzaldehyde, maximum enantioselectivities of 39%, 65%, 99%, 56%, and 62%, respectively, were obtained in the presence of the d-mannitol-based macrocycles as the catalysts.
View Article and Find Full Text PDFSynthesis of l-threitol-based crown ethers and their application as enantioselective phase transfer catalyst in Michael additions.
Chirality
June 2017
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary.
A few new l-threitol-based lariat ethers incorporating a monoaza-15-crown-5 unit were synthesized starting from diethyl l-tartrate. These macrocycles were used as phase transfer catalysts in asymmetric Michael addition reactions under mild conditions to afford the adducts in a few cases in good to excellent enantioselectivities. The addition of 2-nitropropane to trans-chalcone, and the reaction of diethyl acetamidomalonate with β-nitrostyrene resulted in the chiral Michael adducts in good enantioselectivities (90% and 95%, respectively).
View Article and Find Full Text PDFSugar-based novel chiral macrocycles for inclusion applications and chiral recognition.
Carbohydr Res
February 2016
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India. Electronic address:
A convergent template assisted synthesis of sugar-based chiral macrocycles has been achieved. The host-guest inclusion studies have revealed significant interactions of the synthesized macrocycle with primary over secondary ammonium salt. The chiral macrocyle also discriminates between D- and L-phenylalanine methyl ester hydrochlorides as revealed by (1)H NMR spectral studies on the mixture of the host and the guest molecules.
View Article and Find Full Text PDFNitrogen-containing macrocycles having a carbohydrate scaffold.
Adv Carbohydr Chem Biochem
July 2015
Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland. Electronic address:
Nitrogen-containing macrocyclic compounds (amines, amides, and N-heterocyclic derivatives) are important targets in supramolecular chemistry. This chapter discusses the importance of aza-macrocycles in general and, in particular, those receptors containing sugar unit(s). The combination of a carbohydrate scaffold bearing nitrogen-containing functional groups in macrocyclic molecules opens a convenient route to chiral receptors having potentially useful properties.
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