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Optically Active Trialkynyl(phenyl)methane: Synthesis and Determination of Its Absolute Configuration by Vibrational Circular Dichroism (VCD) and Optical Rotatory Dispersion (ORD)
Author(s) -
Buschhaus Boris,
Convertino Vito,
RiveraFuentes Pablo,
AlonsoGómez José Lorenzo,
Petrovic Ana G.,
Diederich François
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000076
Subject(s) - absolute configuration , chemistry , optical rotatory dispersion , vibrational circular dichroism , circular dichroism , enantiomer , dispersion (optics) , optically active , density functional theory , resolution (logic) , enantiomeric excess , chirality (physics) , computational chemistry , crystallography , stereochemistry , organic chemistry , enantioselective synthesis , optics , catalysis , symmetry breaking , chiral symmetry breaking , physics , artificial intelligence , computer science , nambu–jona lasinio model , quantum mechanics
Both enantiomers of an optically active trialkynyl(phenyl)methane (the key building blocks in the construction of a stable expanded cubane) have been prepared. The strategy involved the resolution of a racemic intermediate by means of HPLC on a chiral stationary phase. The absolute configuration of this intermediate was unambiguously assigned by using vibrational circular dichroism (VCD) and optical rotatory dispersion (ORD), in combination with density functional theory (DFT) calculations.