2010European Journal of Organic ChemistryOpen access

Optically Active Trialkynyl(phenyl)methane: Synthesis and Determination of Its Absolute Configuration by Vibrational Circular Dichroism (VCD) and Optical Rotatory Dispersion (ORD)

Boris Buschhaus, Vito Convertino, Pablo Rivera‐Fuentes, José Lorenzo Alonso‐Gómez, Ana G. Petrovic, François Diederich

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Abstract

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.

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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.

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Available abstract

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.

Key concepts: Absolute configuration, Chemistry, Optical rotatory dispersion, Vibrational circular dichroism, Circular dichroism, Enantiomer, Dispersion (optics), Optically active

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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) — Research Paper | ScholarLens