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Late-Stage Functionalization of ( R)-BINOL-Based Diazacoronands and Their Chiral Recognition of α-Phenylethylamine
Agata Tyszka1, Grzegorz Pikus1, Kajetan Dąbrowa1
1Institute of Organic Chemistry , Polish Academy of Sciences , Kasprzaka 44/52 , Warsaw 01-224 , Poland.
Abstract:
Five BINOL-based hosts with a variable macroring size were synthesized in a two-step postfunctionalization protocol by double N-benzylation followed by BMS-mediated reduction of tertiary amide groups (53-93%). UV-vis titration in MeCN reveals that all hosts exhibit a preference for the ( R)-enantiomer over the ( S)-enantiomer of PEA-HCl. The enantioselectivity depends on the number of hydrogen bond (HB) acceptors and the size and flexibility of the macroring. The highest enantiodiscrimination was observed for the 20-membered host 10, containing six HB acceptors ( KR/ KS = 2.13).
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