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Stereochemical significance of O to N atom interchanges within cationic helicenes: experimental and computational evidence of near racemization to remarkable enantiospecificity

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Published in Chemical Science. 2019, vol. 10, no. 29, p. 7059-7067
Abstract Oxygen atoms of cationic dioxa and azaoxa [6]helicenes can be exchanged by amino groups to form azaoxa and diaza [6]helicenes respectively. The mild reaction conditions developed herein allow the construction of libraries of derivatives with sensitive and/or functionalized side chains. Using enantioenriched dioxa or azaoxa helicene precursors, these exchanges lead to either near racemization (es 3%) or to a remarkable enantiospecificity (es up to 97%). This unusual behavior is fully characterized via experimental and computational mechanistic evidence. Based on these investigations, the enantiospecificity of the first transformation can be improved to 57–61%.
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Research groups Groupe Lacour
Groupe Poblador Bahamonde
Groupe Bürgi
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LABRADOR BELTRAN, Maria Géraldine et al. Stereochemical significance of O to N atom interchanges within cationic helicenes: experimental and computational evidence of near racemization to remarkable enantiospecificity. In: Chemical Science, 2019, vol. 10, n° 29, p. 7059-7067. https://archive-ouverte.unige.ch/unige:121523

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Deposited on : 2019-08-12

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