B. Weber, S. Kolczewski, R. Fröhlich
Sep 1, 1999
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0
Influential Citations
11
Citations
Journal
Synthesis
Abstract
The lithio derivatives of (S)and (R)-2-(N,N-dibenzylamino)alkyl carbamates 3 and ent-3, generated by substrate-directed deprotonation from the precursors 2 and ent-2, add with high diastereoselectivity to (S)-2-(N,N-dibenzylamino)alkanals. The (S)aminoaldehyde 5a, derived from (S)-phenylalanine, is produced in situ from the lithium compound 3a by the controlled addition of dioxygen to the reaction mixture affording the protected anti,syn,antiα,δ-diamino-β,γ-diol 6aa which is the core unit of anti-HIV 1 protease agents. Several symmetric and unsymmetric structure analogs, differing in the substitution pattern and the configurations, have been synthesized. A further approach to the title compound is given by the acylation of lithium derivatives 3/4, followed by a hydride reduction. The reaction of the lithium derivatives 3a/4a with CuCl leads to an eliminative oxidative coupling with formation of (3E/Z, 2S,5S)-2,5-dibenzylamino-1,6-diphenylhex-3-enes (E)and (Z)-26.