Abstract
AbstractFour peptidomimics (3–6) containing the cis‐DKP‐1 or trans‐DKP‐2 scaffolds and either L‐Pro or D‐Pro were synthesized. DKP‐1 and DKP‐2 are bifunctional diketopiperazines formally derived from the head‐to‐tail cyclization of L‐aspartic acid and either (R)‐ or (S)‐2,3‐diaminopropionic acid, which feature aminomethyl and carboxymethyl side arms in the 3‐ and 6‐positions of the 2,5‐piperazindione ring. Peptidomimics (3–6) were tested as organocatalysts in the conjugate addition of several aldehydes to β‐nitrostyrene and (E)‐2‐(furan‐2‐yl)nitroethene with good to excellent diastereo‐ and enantioselectivities. Monte Carlo/Energy Minimization (MC/EM) conformational searches were performed on the four catalysts and their enamine derivatives with propanal to rationalize the observed stereoselectivity.
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