Premium
Supramolecular Catalysis of the oxa‐Pictet–Spengler Reaction with an Endohedrally Functionalized Self‐Assembled Cage Complex
Author(s) -
Ngai Courtney,
SanchezMarsetti Colomba M.,
Harman W. Hill,
Hooley Richard J.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202009553
Subject(s) - reactivity (psychology) , supramolecular chemistry , chemistry , aldehyde , catalysis , cage , pictet–spengler reaction , selectivity , combinatorial chemistry , molecule , self assembly , stereochemistry , organic chemistry , medicine , alternative medicine , mathematics , pathology , combinatorics
An endohedrally functionalized self‐assembled Fe 4 L 6 cage complex can catalyze oxa‐Pictet—Spengler cyclizations of tryptophols and various aldehyde derivatives, showing strong rate accelerations and size‐selectivity. Selective molecular recognition of substrates controls the reactivity, and the cage is capable of binding and activating multiple different species along the multistep reaction pathway. The combination of a functionalized active site, size‐selective reactivity, and multistep activation, all from a single host molecule, illustrates the biomimetic nature of the catalysis.