Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics
(Chemical Equation Presented) The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic α-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic α-helix or in terphenyl helix mimetics.
Maity, Prantik,Koenig, Burkhard
supporting information; experimental part
p. 1473 - 1476
(2009/04/10)
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