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Acetylenic Allenophanes: An Asymmetric Synthesis of a Bis(alleno)‐bis(butadiynyl)‐ meta ‐cyclophane
Author(s) -
Clay Matthew D.,
Fallis Alex G.
Publication year - 2005
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.200500484
Subject(s) - allene , cyclophane , chemistry , alkyne , allylic rearrangement , enantiomer , planar chirality , stereochemistry , polymer chemistry , enantioselective synthesis , catalysis , organic chemistry , molecule
A cyclophane with allene and acetylene bridges has been prepared as a single enantiomer. This acetylenic allenophane (see structure) was synthesized by a series of palladium‐ and copper‐mediated coupling reactions. The allene bridge was derived from the ring opening of a chiral epoxy alkyne, which was prepared by a Sharpless asymmetric epoxidation of an allylic alcohol.