Access to the diastereomers of cryptophane cages using HFIP

Cryptophane cages can adopt either an anti or syn configuration that present different recognition properties. While the synthesis of anti -cryptophanes is well reported, the synthesis of syn -cryptophanes remains a challenge. Herein, we demonstrate that the use of HFIP as a co-solvent during the se...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-03, Vol.58 (2), p.333-3333
Main Authors: Della-Negra, Oriane, Cirillo, Yoann, Brotin, Thierry, Dutasta, Jean-Pierre, Saaidi, Pierre-Loic, Chatelet, Bastien, Martinez, Alexandre
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Summary:Cryptophane cages can adopt either an anti or syn configuration that present different recognition properties. While the synthesis of anti -cryptophanes is well reported, the synthesis of syn -cryptophanes remains a challenge. Herein, we demonstrate that the use of HFIP as a co-solvent during the second ring closure reaction significantly affects the regioselectivity, providing easier access to the syn -cryptophane stereomers. The use of the HFIP/bisulfate salt combination provides convenient and fast access to syn -cryptophanes.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06607b