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

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Abstract
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.

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