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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

Published inChemical Science, vol. 10, no. 29, p. 7059-7067
Publication date2019
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%.

Citation (ISO format)
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. doi: 10.1039/C9SC02127B
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ISSN of the journal2041-6520
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Creation08/09/2019 2:36:00 PM
First validation08/09/2019 2:36:00 PM
Update time03/15/2023 5:50:44 PM
Status update03/15/2023 5:50:43 PM
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