Acetylenic Allenophanes: An Asymmetric Synthesis of a Bis(alleno)‐bis(butadiynyl)‐ meta ‐cyclophane | Zendy

Clay Matthew D. | Zendy; Fallis Alex G. | Zendy

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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.

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