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A Modular Synthesis of Multidentate S‐, N‐ and O‐Containing Meta‐ and Paracyclophanes
Author(s) -
Rasheed Omer K.,
Bailey Patrick D.,
Lawrence Amy,
Quayle Peter,
Raftery James
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501058
Subject(s) - thioether , chemistry , regioselectivity , alkylation , pyridine , chirality (physics) , ring (chemistry) , stereochemistry , nucleophile , denticity , enantioselective synthesis , combinatorial chemistry , modular design , alanine , amino acid , organic chemistry , catalysis , crystal structure , chiral symmetry breaking , physics , quantum mechanics , computer science , nambu–jona lasinio model , operating system , quark , biochemistry
The development of a modular approach to macrocycle assembly has enabled the synthesis of a library of pyridine‐based macrocycles possessing multiple donor sites where chirality was readily introduced from ( R )‐ or ( S )‐alanine, a representative amino acid. The facile, regioselective, nucleophilic ring opening of aziridines by dithiols enabled the synthesis of thioether‐based linkers which on subsequent alkylation provided access to optically pure macrocycles.