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ChemInform Abstract: Asymmetric Mannich Synthesis of β-Amino Acids with Two New Stereogenic Centers at the α and β Positions.

✍ Scribed by H. KUNZ; A. BURGARD; D. SCHANZENBACH

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199722215

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✦ Synopsis

Asymmetric Mannich Synthesis of β-Amino Acids with Two New Stereogenic Centers at the α and β Positions. -The ZnCl2-catalyzed Mannich reaction of N-galactosyl aldimines, e.g. ( I), with ketene acetals as the C-nucleophiles furnishes β-amino acid derivatives, important building blocks of natural products and drugs. The bis(silyl) ketenes (II) lead to formation of erythro diastereomers (III), while threo diastereomers, e.g. (V), are formed using lithium ester enolates (IV).

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