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Cyclobutane amino acids (CBAAs): asymmetric Strecker synthesis of enantiopure cis- and trans-2,4-methanovalines

✍ Scribed by Franz-J. Volk; Marita Wagner; August W. Frahm

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 235 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(02)00868-6

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✦ Synopsis

Synthesis of enantiopure 2,4-methanovalines has been achieved by means of asymmetric Strecker synthesis starting from racemic 2-methylcyclobutanone. The trans-configured a-amino acids were obtained from cyanide additions carried out in methanol, whereas the cis-configured 2,4-methanovalines were accessible via reactions in hexane. Relative stereochemistry was elucidated from NOESY experiments, while absolute configurations were assigned from X-ray crystallographic analysis.

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