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(S)-Pyroglutamic Acid, (S)-Malic Acid, and (S)-Serine as Useful Starting Materials in the Synthesis of Enantiopure Hydroxyamidines (2000)

Ostendorf, Martin ; Dĳkink, Jan ; Rutjes, Floris P. J. T. ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 115-124

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ISSN: 1434-193X

Keywords: Amidines ; Chiral bases ; N-Acyliminium ions ; Enantioselective catalysis ; Chiral pool ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---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.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

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