Synthesis 2016; 48(24): 4589-4593
DOI: 10.1055/s-0036-1588596
paper
© Georg Thieme Verlag Stuttgart · New York

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

Suyog Marathe
Department of Chemistry, University of Mumbai, Vidyanagari, Kalina, Santacruz (E), Mumbai – 400 098, India   Email: avkarnik@chem.mu.ac.in
,
Anil V. Karnik*
Department of Chemistry, University of Mumbai, Vidyanagari, Kalina, Santacruz (E), Mumbai – 400 098, India   Email: avkarnik@chem.mu.ac.in
› Author Affiliations
Further Information

Publication History

Received: 08 July 2016

Accepted after revision: 26 August 2016

Publication Date:
19 September 2016 (online)


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.

Supporting Information

 
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