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Royal Society of Chemistry, Chemical Science, 29(10), p. 7059-7067, 2019

DOI: 10.1039/c9sc02127b

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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

Journal article published in 2019 by Geraldine M. Labrador ORCID, Céline Besnard ORCID, Thomas Bürgi ORCID, Amalia I. Poblador-Bahamonde ORCID, Johann Bosson ORCID, Jérôme Lacour ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Oxygen atoms of cationic dioxa and azaoxa [6]helicenes can be exchanged by amino groups and these reactions lead to either near racemization (es 3%) or to a remarkable enantiospecificity (es up to 97%). Based on detailed investigations, the chirality transfer of the first transformation can be improved to 61%.