SPALLAROSSA , Martina

The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehydes and 2,6-disubstituted aromatic aldehydes, whereas Z-olefins were formed predominantly...

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Complex polycyclic compounds resembling some natural alkaloids have been prepared in only three high yielding steps by combining the Ugi or Passerini multicomponent reactions with two metal-catalyzed cyclizations: an intramolecular Tsuji–Trost reaction of the isocyanide-derived amide followed by a ring-closing metathesis. Scaffold diversity may...

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Enantiomerically pure 4,5-dihydro-1H-benzo[c]azepines with three contiguous stereogenic centers have been assembled by convergent strategy with a good control of diastereoselectivity. The two steps are as follows: an asymmetric organocatalytic Mannich reaction performed on Boc-imines of o-(azidomethyl)benzaldehydes, followed by a one-pot...

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The purpose of this study was to explore a series of Passerini reactions on a biocatalytically derived enantiopure azetidine-2-carboxyaldehyde in order to obtain, in a diastereoselective manner, polyfunctionalised derivatives having the potential to be cyclized to chiral bridged bicyclic nitrogen heterocycles. While diastereoselectivity was...

Isocyanide-based multicomponent reactions (IMCRs) are a very useful tool for the rapid assembly of libraries of drug-like heterocycles, with the introduction of 3-4 diversity inputs. However, the stereocontrolled obtainment of complex products endowed with several stereogenic centres is still challenging because of: a) scarce availability of...