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Chiral Recognition of ( R )‐(−)‐1,7‐Dioxaspiro‐[5.5]undecane by Hexakis(2,3,6‐tri‐ O ‐methyl)‐α‐cyclodextrin
Author(s) -
Yannakopoulou Konstantina,
Mentzafos Dimitris,
Mavridis Irene M.,
Dandika Konstantina
Publication year - 1996
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.199624801
Subject(s) - undecane , cyclodextrin , enantiomer , chemistry , aqueous solution , inclusion compound , stereochemistry , medicinal chemistry , organic chemistry
Even on a large scale an aqueous solution of 1,7‐dioxaspiro[5.5]undecane and a tailored cyclodextrin selectively yields the inclusion complex with the ( R ) guest (shown on the right), the structure of which was studied both in the solid state and in solution. The yields are higher than would be expected for the racemate because the ( S ) enantiomer of the guest is transformed into the ( R ) enantiomer, which forms the more stable host–guest complex.