Bifunctional 2,5-Diketopiperazines as Efficient Organocatalysts for the Enantioselective Conjugate Addition of Aldehydes to Nitroolefins
Articolo
Data di Pubblicazione:
2011
Citazione:
Bifunctional 2,5-Diketopiperazines as Efficient Organocatalysts for the
Enantioselective Conjugate Addition of Aldehydes to Nitroolefins / M. Durini, F.A. Sahr, M. Kuhn, M. Civera, C.M.A. Gennari, U. Piarulli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2011:28(2011), pp. 5599-5607. [10.1002/ejoc.201100794]
Abstract:
Four 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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Diketopiperazines; Michael addition; Nitroolefins; Organocatalysis; Peptidomimetics
Elenco autori:
M. Durini, F.A. Sahr, M. Kuhn, M. Civera, C.M.A. Gennari, U. Piarulli
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