Alkylation of Amino Acids without Loss of Optical Activity: α- and β-Alkylation of an Aspartic Acid Derivative

Authors

  • Prof. Dr. Dieter Seebach,

    Corresponding author
    1. Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
    • Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
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  • Dipl. sc. nat. Daniel Wasmuth

    1. Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
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  • Dedicated to Professor Leopold Horner on the occasion of his 70th birthday

Abstract

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The α-alkylation of β-heterosubstituted carbonyl compounds leads to a surprising result in the case of L-(+)-N-formylaspartic acid di-tert-butyl ester: A mixture of the β- and α-substituted aspartic acid derivatives (1) and (2) (ca. 7:2) is obtained. The erythro-isomers of (1) are formed stereospecifically, while, interestingly, an enantiomer of (2) is formed in excess; R[DOUBLE BOND]CH3, C2H5, CH2CH[DOUBLE BOND]CH2, CH2C6H5.

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