A Modular Synthesis of Multidentate S-, N- and O-Containing Meta- and Paracyclophanes

Journal article


Rasheed, OK, Bailey, PD, Lawrence, A, Quayle, P and Raftery, J (2015). A Modular Synthesis of Multidentate S-, N- and O-Containing Meta- and Paracyclophanes. European Journal of Organic Chemistry. 2015 (32), pp. 6988 - 6993.
AuthorsRasheed, OK, Bailey, PD, Lawrence, A, Quayle, P and Raftery, J
Abstract

© 2015 Wiley-VCH Verlag GmbH andCo. KGaA, Weinheim. 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. A modular approach to macrocyclic assembly has enabled the synthesis of a library of macrocycles possessing multiple donor sites where chirality was readily introduced from (S)-alanine. Key to this approach was the facile, regioselective, nucleophilic ring opening of aziridines by dithiols followed by macrocylisation under conditions of high dilution.

Year2015
JournalEuropean Journal of Organic Chemistry
Journal citation2015 (32), pp. 6988 - 6993
PublisherWiley-VCH
ISSN1434-193X
Digital Object Identifier (DOI)doi:10.1002/ejoc.201501058
Publication dates
Print01 Nov 2015
Publication process dates
Deposited31 Oct 2016
Accepted14 Aug 2015
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All rights reserved - not available for copyright reasons
Supplemental file
License
CC BY 4.0
File description
Supporting Information
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