Synthesis of C ₂-Symmetric Isoxazole-Fused BINOL: An Entry to Sterically Crowded Atropisomeric Systems

Abstract

A fluorescence-active modified BINOL with heteroaromatic fused rings containing two different heteroatoms is synthesized in good yield. Its racemate form is well characterized by chiral HPLC analysis. The molecule bears sterically hindered geometry and has potential for stereochemical properties normally exhibited by BINOLs. The molecule has two ends with different ligating atoms in the form of hydroxy groups at one end and isoxazole ring heteroatoms on the other end. This feature may be useful for molecular recognition of both hard and soft cations.

Key words

axial chirality - BINOL - BINAP - strategic cyclization - isoxazole-fused BINOL - oxidative coupling - chiral HPLC - fluorescence-active

• References

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