Homo-Freidinger Lactams: Stereoselective Synthesis of 4-Aminopiperidin-2-one Derivatives from Aspartic Acid

Klaus Weber; Peter Gmeiner

doi:10.1055/s-1998-1786

Synlett 1998; 1998(8): 885-887
DOI: 10.1055/s-1998-1786

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Homo-Freidinger Lactams: Stereoselective Synthesis of 4-Aminopiperidin-2-one Derivatives from Aspartic Acid

Klaus Weber^* , Peter Gmeiner

^*Institut für Pharmazie und Lebensmittelchemie der Universität Erlangen-Nürnberg, Schuhstraße 19, D-91052 Erlangen, Germany; Fax + 49(9131)85 25 85; E-mail: gmeiner@pharmazie.uni-erlangen.de

Abstract

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Starting from aspartic acid a stereoselective synthesis of enantiomerically pure 4-aminopiperidin-2-ones which can serve as conformationally restrained β-amino acid equivalents in peptidomimetics is described. The synthesis is based on the regioselective functionalization of the 1,4-bis-electrophile 2b and a diastereoselective introduction of various side chain equivalents into the lactam-α-position of 4b, c.

aspartic acid - regioselective functionalization - diastereoselective alkylation - peptidomimetic - Homo-Freidinger lactam

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