247575-93-5Relevant academic research and scientific papers
Facile and highly stereoselective synthesis of the C2-symmetrical diamino diol core-unit of HIV-1 protease inhibitors and of their symmetrical and unsymmetrical analogs from lithiated 2-(dibenzylamino)alkyl carbamates: Oxidative dimerization
Weber,Kolczewski,Fr?hlich,Hoppe
, p. 1593 - 1606 (2007/10/03)
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,anti-α,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 (3 E/Z, 2S,5S)-2,5-dibenzylamino-1,6- diphenylhex-3-enes (E)- and (Z)-26.
