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Foldamer‐Mediated Remote Stereocontrol: >1,60 Asymmetric Induction
Author(s) -
Byrne Liam,
Solà Jordi,
Boddaert Thomas,
Marcelli Tommaso,
Adams Ralph W.,
Morris Gareth A.,
Clayden Jonathan
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201308264
Subject(s) - foldamer , iminium , dimer , chemistry , stereochemistry , asymmetric induction , helix (gastropod) , alkene , amino acid , terminal (telecommunication) , enantioselective synthesis , ion , catalysis , organic chemistry , biochemistry , computer science , ecology , snail , biology , telecommunications
An N‐terminal L ‐α‐methylvaline dimer induces complete conformational control over the screw sense of an otherwise achiral helical peptide foldamer formed from the achiral quaternary amino acids Aib and Ac 6 c. The persistent right‐handed screw‐sense preference of the helix enables remote reactive sites to fall under the influence of the terminal chiral residues, and permits diastereoselective reactions such as alkene hydrogenation or iminium ion addition to take place with 1,16‐, 1,31‐, 1,46‐ and even 1,61‐asymmetric induction. Stereochemical information may be communicated in this way over distances of up to 4 nm.