Alessandra Lattanzi

Publications (76) View all

• Article: Asymmetric organocatalysis mediated by α,α-l-diaryl prolinols: recent advances.

  Sara Meninno, Alessandra Lattanzi
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  ABSTRACT: This feature article illustrates progress in asymmetric organocatalysis achieved by using readily available α,α-l-diaryl prolinols from 2009 up to middle 2012. This class of bifunctional organocatalysts has shown the ability to catalyze a variety of reactions such as epoxidation, cyclopropanation, α-sulfenylation of active methines, cross conjugate addition, direct aldol, cycloaddition and desymmetrization reactions. The most striking feature of these promoters is to enable either non-covalent or covalent activation of the reagents, thus distinguishing themselves as a rare example of organic promoters capable of encompassing alternative mechanistic pathways, namely enamine/iminium catalysis and Brønsted acid/base catalysis.
  Chemical Communications 04/2013; · 6.17 Impact Factor
• Article: Enantioselective α-hydroxylation of β-ketoamides.

  Claudia De Fusco, Sara Meninno, Consiglia Tedesco, Alessandra Lattanzi
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  ABSTRACT: The first enantioselective α-hydroxylation reaction of α-substituted β-ketoamides has been developed by using the commercially available hydroquinine/TBHP system. The tertiary alcohols are obtained in good to high yield and up to 83% ee, which can be improved by a single crystallization.
  Organic & Biomolecular Chemistry 01/2013; · 3.70 Impact Factor
• Article: Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center.

  Claudia De Fusco, Tiziana Fuoco, Gianluca Croce, Alessandra Lattanzi
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  ABSTRACT: A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.
  Organic Letters 08/2012; 14(16):4078-81. · 5.86 Impact Factor
• Article: Highly enantioselective epoxidation catalyzed by cinchona thioureas: synthesis of functionalized terminal epoxides bearing a quaternary stereogenic center.

  Alessio Russo, Gerardina Galdi, Gianluca Croce, Alessandra Lattanzi
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  ABSTRACT: A brilliant debut! Cinchona thioureas have been reported for the first time as catalysts in the area of asymmetric oxidations. They efficiently promote an unprecedented highly enantioselective epoxidation of deactivated 1,1-disubstituted alkenes to terminal epoxides containing a quaternary stereogenic center (see scheme).
  Chemistry 04/2012; 18(20):6152-7. · 5.93 Impact Factor
• Article: Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction.

  Alessandra Lattanzi, Claudia De Fusco, Alessio Russo, Albert Poater, Luigi Cavallo
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  ABSTRACT: A dramatic enhancement of the diastereo- and enantioselectivity in the nitro-Michael addition reaction organocatalysed by a commercially available α,α-L-diaryl prolinol was disclosed when performing the reaction in unconventional hexafluorobenzene as a medium. DFT calculations were performed to clarify the origin of stereoselectivity and the role of C(6)F(6).
  Chemical Communications 12/2011; 48(11):1650-2. · 6.17 Impact Factor