(R)-(+) and (S)-()-1-phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2, 3-butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2-hydroxy-3- nitrocyclopentanone derivatives. The reactions were carried out both in solvent and under solventfree conditions. The absolute configurations of the products were assigned by X-ray and circular dichroism spectra analyses.
Optically Active α-Phenylethylamine as Efficient Organocatalyst in the Solvent-free Reactions Between 2,3-Butanedione and Conjugated Nitroolefins / F., Felluga; C., Forzato; P., Nitti; G., Pitacco; Prati, Fabio; E., Valentin; E., Zangrando. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 24:(2012), pp. 1005-1012. [10.1002/chir.22088]
Optically Active α-Phenylethylamine as Efficient Organocatalyst in the Solvent-free Reactions Between 2,3-Butanedione and Conjugated Nitroolefins
PRATI, Fabio;
2012
Abstract
(R)-(+) and (S)-()-1-phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2, 3-butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2-hydroxy-3- nitrocyclopentanone derivatives. The reactions were carried out both in solvent and under solventfree conditions. The absolute configurations of the products were assigned by X-ray and circular dichroism spectra analyses.
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