Enantioselective Complexation of Flexible and Rigid Substrates through Molecular Recognition

Michael Famulok, Kyu‐Sung ‐S Jeong, Ghislain Deslongchamps, Julius Rebek

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)


Up to four hydrogen bonds are formed on complexation of hydantoins by 2,7‐naphthyl‐bridged dilactams. The L‐hydantoins (R may be CH2Ph, and CH(CH3)2, for example) bind preferentially to the (–)‐enantiomer of the receptor (ΔΔG = −0.6 kcal mol−1). Similarly, this enantioselectivity is observed in the complexation of L‐hydroorotic acid methyl ester. The selectivity of the binding of dipeptides, which are substantially more flexible, is less pronounced. (Figure Presented.)

Original languageEnglish
Pages (from-to)858-860
Number of pages3
JournalAngewandte Chemie International Edition in English
Issue number7
Publication statusPublished - 1991 Jul

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry


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