2009
DOI: 10.1016/j.tet.2009.06.039
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Synthesis, optical resolution and absolute configuration of inherently chiral calixarene carboxylic acids

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Cited by 30 publications
(18 citation statements)
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“…A complimentary strategy employed by Kalchenko and co‐workers has been to install the chiral auxiliary distal to the monoalkyl group ( 8 ) and then explore mono‐acylation/alkylation towards ICCs (Scheme ) . This method has not been exhaustively studied, but the diastereoselective outcome is sensitive to both the chiral auxiliary and the electrophile used.…”
Section: Upper‐ and Lower‐rim Functionalisationmentioning
confidence: 99%
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“…A complimentary strategy employed by Kalchenko and co‐workers has been to install the chiral auxiliary distal to the monoalkyl group ( 8 ) and then explore mono‐acylation/alkylation towards ICCs (Scheme ) . This method has not been exhaustively studied, but the diastereoselective outcome is sensitive to both the chiral auxiliary and the electrophile used.…”
Section: Upper‐ and Lower‐rim Functionalisationmentioning
confidence: 99%
“…Other chiral auxiliaries examined include the camphorsulfonyl group already mentioned, which failed to react with the isocyanate, and menthyl‐bromoacetate which gave no diastereoselectivity in the subsequent acylation reaction . Other isocyanates have been used, but give lower diastereoselectivity, as do p ‐toluenesulfonyl chloride and benzoyl chloride . The method has, however, been used successfully to synthesise an ICC carboxylic acid that showed chiral discrimination towards l ‐ and d ‐α‐phenylethylamine by 1 H NMR spectroscopy …”
Section: Upper‐ and Lower‐rim Functionalisationmentioning
confidence: 99%
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“…In this aspect both enantiomers of inherently chiral calixarenecarboxylic acids 207a and 207b with ABCD substitution patterns have been prepared. 139 Calixarene 208 was reacted with (R+)-N-(α-phenylethyl)bromoacetamide affording calixarene 209 and benzoylation of one its hydroxyl groups leads to the mixture of paco diastereomers 210a and 210b. Diastereotopicity of 210a and 210b results both from the presence of the chiral carbon atom of phenylethylamide group and of the ABCD asymmetrical substitution of the calixarene macrocycle.…”
Section: Scheme 54mentioning
confidence: 99%