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Enantioselective Complexation of Flexible and Rigid Substrates through Molecular Recognition
Author(s) -
Famulok Michael,
Jeong KyuSung,
Deslongchamps Ghislain,
Rebek Julius
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199108581
Subject(s) - hydrogen bond , enantiomer , enantioselective synthesis , chemistry , selectivity , molecular recognition , stereochemistry , molecule , organic chemistry , catalysis
Up to four hydrogen bonds are formed on complexation of hydantoins by 2,7‐naphthyl‐bridged dilactams. The L ‐hydantoins (R may be CH 2 Ph, and CH(CH 3 ) 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.