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Sulfoxides in the allylation of aldehydes in the presence of silicon tetrachloride and allyltributylstannane

100%
Massa A., Capozzolo L., Scettri A.
Open Chemistry
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2010
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vol. 8
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issue 6
1210-1215
EN
SiCl4 can be conveniently activated by catalytic amounts of dimethyl sulfoxide or other readily-available sulfoxides for the allylation of aromatic, hetero-aromatic and unsaturated aldehydes in the presence of allyltributyl stannane. Chiral aryl methyl sulfoxides have been used to develop asymmetric allylation methods, as well as probe the aldehyde substrate scope.
2
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Mukaiyama-Michael vinylogous additions to nitroalkenes under solvent-free conditions

100%
Scettri A., Villano R., Manzo P., Acocella M.
Open Chemistry
|
2012
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vol. 10
|
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

100%
Villano R., Acocella M., Sio V., Scettri A.
|
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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