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An Enantiomerically Pure Alleno‐Acetylenic Macrocycle: Synthesis and Rationalization of Its Outstanding Chiroptical Response
Author(s) -
AlonsoGómez José Lorenzo,
RiveraFuentes Pablo,
Harada Nobuyuki,
Berova Nina,
Diederich François
Publication year - 2009
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.200901240
Subject(s) - rationalization (economics) , circular dichroism , optically active , chemistry , stereochemistry , organic chemistry , philosophy , epistemology
The unique combination of geometric and electronic properties explains the remarkable magnitude of the Cotton effects in the circular dichroism spectra of new enantiomerically pure alleno‐acetylenic macrocycles (see picture). The macrocycles ( P , P , P , P )‐(−)‐ 1 (red) and ( M , M , M , M )‐(+)‐ 1 (blue) were prepared in three steps starting from optically pure 1,3‐di‐ tert ‐butyl‐1,3‐diethynylallenes.