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We have achieved the enantioselective synthesis of axially chiral figure-eight spiro[9.9]cycloparaphenylene (CPP) tetracarboxylates with up to 75:25 er via the cationic Rh(I)/(R)-H8-BINAP complex-catalyzed chemo-, regio-, and enantioselective intermolecular double [2… Click to show full abstract
We have achieved the enantioselective synthesis of axially chiral figure-eight spiro[9.9]cycloparaphenylene (CPP) tetracarboxylates with up to 75:25 er via the cationic Rh(I)/(R)-H8-BINAP complex-catalyzed chemo-, regio-, and enantioselective intermolecular double [2 + 2 + 2] cycloaddition of an achiral symmetric tetrayne with dialkyl acetylenedicarboxylates followed by reductive aromatization. The spiro[9.9]CPP tetracarboxylates are highly distorted at the phthalate moieties with large dihedral and boat angles and exhibit weak aggregation-induced emission enhancement behavior.
Journal Title: Organic letters
Year Published: 2023
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