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Tetrahedron-asymmetry | 2001

Conjugate addition of hydroxylamino derivatives to alkylidene malonates in the presence of chiral Lewis acids

Giuliana Cardillo; Luca Gentilucci; Massimo Gianotti; Hahn Kim; Rossana Perciaccante; Alessandra Tolomelli

Abstract The conjugate addition of O -benzylhydroxylamine and N , O -bis(trimethylsilyl)hydroxylamine to alkylidene and arylidene malonates in the presence of Lewis acids affords the corresponding β-hydroxylamino derivatives in good yields. The use of Cu(OTf) 2 in the presence of chiral bisoxazoline ligands opens the possibility of performing this reaction in a catalytic and enantioselective way.


Tetrahedron-asymmetry | 2002

Enantioselective synthesis of aziridine 2,2-dicarboxylates. Part II: Determination of the absolute configuration

Giuliana Cardillo; Serena Fabbroni; Luca Gentilucci; Massimo Gianotti; Rossana Perciaccante; Simona Selva; Alessandra Tolomelli

Abstract The absolute configuration of aziridine-2,2-dicarboxylates was determined through their transformation into the corresponding diastereomeric (S)-(−)-α-methylbenzylamido derivatives. The data obtained allows establishment of the stereochemistry of the first step of the conjugate addition reaction catalyzed by chiral bisoxazoline–Cu complex.


Chemical Communications | 2001

Design of boron bis-oxazolinate (B-BOXate) complexes: a new class of stable organometallic catalysts

Marco Bandini; Pier Giorgio Cozzi; Magda Monari; Rossana Perciaccante; Simona Selva; Achille Umani-Ronchi

A new class of remarkably stable B-BOXate complexes has been synthesised, isolated and employed as chiral catalysts for asymmetric reduction of variously substituted prochiral ketones.


Chemical Communications | 2018

Application of coumarin dyes for organic photoredox catalysis

Andrea Gualandi; Giacomo Rodeghiero; Emanuele Della Rocca; Francesco Bertoni; Marianna Marchini; Rossana Perciaccante; Thomas Paul Jansen; Paola Ceroni; Pier Giorgio Cozzi

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.


Organic Letters | 2005

Highly diastereoselective allylic azide formation and isomerization. Synthesis of 3(2'-amino)-beta-lactams.

Giuliana Cardillo; Serena Fabbroni; Luca Gentilucci; Rossana Perciaccante; Fabio Piccinelli; Alessandra Tolomelli


Journal of Organic Chemistry | 2001

Synthesis of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-(bistrimethylsilyl)hydroxylamine to alpha,beta-unsaturated malonates.

Giuliana Cardillo; Luca Gentilucci; Massimo Gianotti; Rossana Perciaccante; Alessandra Tolomelli


Tetrahedron-asymmetry | 2004

α-Bromo-β,γ-unsaturated ketenes for the synthesis of α-benzylamino-β,γ-unsaturated acids

Giuliana Cardillo; Serena Fabbroni; Luca Gentilucci; Rossana Perciaccante; Alessandra Tolomelli


Tetrahedron | 2004

Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition

Giuliana Cardillo; Serena Fabbroni; Luca Gentilucci; Rossana Perciaccante; Fabio Piccinelli; Alessandra Tolomelli


Journal of Organic Chemistry | 2006

Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening

Fides Benfatti; Giuliana Cardillo; Luca Gentilucci; Rossana Perciaccante; Alessandra Tolomelli; Alberico Catapano


Tetrahedron-asymmetry | 2006

Synthesis of enantiomerically pure αvβ3 integrin ligands based on a 5,6-dihydropyridin-2-one scaffold

Fides Benfatti; Giuliana Cardillo; Serena Fabbroni; Luca Gentilucci; Rossana Perciaccante; Alessandra Tolomelli; Monica Baiula; Santi Spampinato

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