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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)

✍ Scribed by Boris Buschhaus; Vito Convertino; Pablo Rivera-Fuentes; José Lorenzo Alonso-Gómez; Ana G. Petrovic; François Diederich


Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
333 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis


Abstract

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.