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Mukaiyama-Michael vinylogous additions to nitroalkenes under solvent-free conditions

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Scettri A., Villano R., Manzo P., Acocella M.
Open Chemistry
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2012
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vol. 10
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issue 1
47-53
EN
The first Mukaiyama-Michael vinylogous reaction of a dioxinone-derived silyl ether to nitroalkenes is reported. The conjugate addition is performed in absence of any catalyst under solvent-free conditions, proceeding with satisfactory efficiency with variously substituted nitroalkenes. Moreover, the first organocatalyzed Mukaiyama-Michael vinylogous reaction of trimethylsilyloxyfuran to nitroalkenes is described.The reaction is promoted by Brønsted acids under solvent-free conditions, taking place in moderate to good yield with variously substituted nitroalkenes..
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1-Naphthyl-TADDOL/Emim BF4: A new catalytic system for the asymmetric addition of Chan’s diene to aromatic aldehydes

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Villano R., Acocella M., Sio V., Scettri A.
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EN
A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan’s diene to aldehydes under solvent-free conditions. This new organocatalyst generated in situ by mixing 1-naphthyl-TADDOL derivative and Emim BF4 was able to give enantioenriched vinylogous aldols and hetero-Diels-Alder cycloadducts. A mechanistic investigation through the detection of nonlinear effects confirmed the involvement of the ionic liquid in the formation of a new catalytic supramolecular species.
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