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.

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]

Bifunctional 2,5-Diketopiperazines as Efficient Organocatalysts for the Enantioselective Conjugate Addition of Aldehydes to Nitroolefins

M. Civera;C.M.A. Gennari
Penultimo
;
2011

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.
Diketopiperazines; Michael addition; Nitroolefins; Organocatalysis; Peptidomimetics
Settore CHIM/06 - Chimica Organica
2011
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/162014
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