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Convergent Synthesis, Resolution, and Chiroptical Properties of Dimethoxychromenoacridinium Ions

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posted on 18.07.2014, 00:00 by Jérôme Gouin, Thomas Bürgi, Laure Guénée, Jérôme Lacour
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 (−)-(M) and (+)-(P) enantiomers can be separated by chiral stationary-phase chromatography. Determination of the absolute configuration and racemization barrier (ΔG (433 K) 33.3 ± 1.3 kcal·mol–1) was achieved by VCD and ECD spectroscopy, respectively.