Convergent Synthesis, Resolution, and Chiroptical
Properties of Dimethoxychromenoacridinium Ions
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Abstract
Cationic azaoxa[4]helicenes can be
prepared in a single step from
a common xanthenium precursor by addition of nucleophilic amines under
monitored conditions (160 °C, 2 min, MW). The (−)-(<i>M</i>) and (+)-(<i>P</i>) enantiomers can be separated
by chiral stationary-phase chromatography. Determination of the absolute
configuration and racemization barrier (Δ<i>G</i><sup>⧧</sup> (433 K) 33.3 ± 1.3 kcal·mol<sup>–1</sup>) was achieved by VCD and ECD spectroscopy, respectively