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Asymmetric Allenophanes: Synthesis of a Tris‐ meta ‐allenophane and Tetrakis‐ meta ‐allenophane by Sequential Cross‐Coupling
Author(s) -
Leclère Mathieu,
Fallis Alex G.
Publication year - 2008
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.200703003
Subject(s) - allene , enantioselective synthesis , sonogashira coupling , chemistry , propargyl , combinatorial chemistry , tris , coupling (piping) , stereochemistry , catalysis , organic chemistry , palladium , materials science , biochemistry , metallurgy
Around and around : A strategy based on sequential Pd‐catalyzed cross‐coupling reactions was applied for the asymmetric synthesis of new macrocyclic meta ‐allenophanes composed of 18‐ or 24‐membered rings (see structures). The chiral components, tertiary propargyl alcohols and allene bridges, were assembled by a general enantioselective protocol, which involved a Sharpless epoxidation, an oxidation, and Sonogashira cross‐coupling.