25‐Propyloxy‐26,27‐dibenzoyloxy‐calix[4]arene as Precursor for the Synthesis of Inherently Chiral Calixarenes

This paper shows that 25‐propyloxy‐26,27‐dibenzoyloxy‐calix[4]arene can be a convenient precursor for the formation of inherently chiral configuration on the calixarene platform. The methods for sequential regioselective debenzoylation and electrophilic substitution on the upper rim were developed....

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Bibliographic Details
Published in:European journal of organic chemistry 2021-07, Vol.2021 (28), p.3912-3919
Main Authors: Trybrat, Oleksandr O., Yesypenko, Oleksandr A., Shishkina, Svitlana V., Rusanov, Eduard B., Karpichev, Yevgen A., Kalchenko, Vitaly I.
Format: Article
Language:English
Subjects:
Electrophilic substitution
Hydrolysis
Inherently chiral calix
Optical resolution
Selective debenzoylation
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Summary:This paper shows that 25‐propyloxy‐26,27‐dibenzoyloxy‐calix[4]arene can be a convenient precursor for the formation of inherently chiral configuration on the calixarene platform. The methods for sequential regioselective debenzoylation and electrophilic substitution on the upper rim were developed. The inherently chiral calix[4]renes with two and three different functional groups on the upper rim were synthesized. 25‐Propyloxy‐26,27‐dibenzoyloxy‐calix[4] is a convenient precursor for the formation of inherently chiral configuration on the calixarene platform. The synthesis of inherently chiral calixarenes with one, two and three different functional groups on the upper rim was described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100624