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Selective Micellar Catalysis with Histidinyl Surfactants of Defined Absolute Configuration
Author(s) -
Brown John M.,
Elliott Richard L.,
Griggs Colin G.,
Helmchen Günter,
Nill Günter
Publication year - 1981
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.198108901
Subject(s) - diastereomer , absolute configuration , hydrolysis , stereoselectivity , chemistry , catalysis , pulmonary surfactant , absolute (philosophy) , organic chemistry , stereochemistry , medicinal chemistry , biochemistry , philosophy , epistemology
The stereoselectivity of the micellar‐catalyzed hydrolysis of amino acid esters (2) by the histidinyl surfactants (1) strongly depends on their absolute configuration: In presence of the R , S ‐configurated surfactant (1) , which like the S , S ‐diastereomer was also prepared in a few steps from γ‐butyrolactone, S ‐ (2) hydrolyzes 2.5 times as fast as R ‐ (2) .