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( S )‐Pyroglutamic Acid, ( S )‐Malic Acid, and ( S )‐Serine as Useful Starting Materials in the Synthesis of Enantiopure Hydroxyamidines
Author(s) -
Ostendorf Martin,
Dijkink Jan,
Rutjes Floris P. J. T.,
Hiemstra Henk
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j
Subject(s) - chemistry , enantiopure drug , amidine , malic acid , racemization , diastereomer , pyroglutamic acid , serine , tautomer , stereochemistry , organic chemistry , medicinal chemistry , enantioselective synthesis , amino acid , catalysis , biochemistry , citric acid , enzyme
The synthesis of four enantiopure hydroxyamidines is described. One amidine was obtained from ( S )‐pyroglutamic acid. Its key step involved the addition of phenylmagnesium bromide to the corresponding ester, affording the tertiary alcohol without detectable racemization. The second amidine was obtained by coupling of an ( S )‐malic acid derived N ‐acyliminium ion with β‐naphthol. The other amidines were obtained from an ( S )‐serine‐derived imide which was reduced to two diastereomeric lactams that were eventually transformed into the corresponding amidines.