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Asymmetric Synthesis Lab

We enjoy playing with Asymmetric Synthesis. Our ambition is to control the spatial arrangement of stereogenic centers and axes using organo- and metal catalyzed reactions. Our research fields are oriented to the study of asymmetric vinylogous reactions and the development of processes which enables the enantioselective synthesis of atropisomers.

Organocatalytic enantioselective formation of atropisomers:

  • Enantioselective organocatalysis has been successfully applied to the synthesis of atropisomers

  • Desymmetrization of N-arylmaleimmides by nucleophilic attack on their prochiral double bond afforded atropisomeric succinimides 

  • Axially chiral cyclohexylidene oxindoles were selectively obtained by means of organocatalytic  Knoevenagel condensation. Insights on the mechanism were obtained by DFT methods.

DFT calculations

  • Computational studies for the comprehension of the reaction mechanisms
  • Catalyst design
  • Conformational analysis

New organocatalytic enantioselective vinylogous reactions:

  • Vinylogous reactivity is a valuable strategy for the remote modification of a molecule.

  • Vinylogous addition of alkylidene oxindole on aryl trifluoromethyl ketone resulted in a rare aldol reaction-lactonization cascade. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient entry to enantioenriched trifluoromethylated α,β-unsaturated δ-lactones.

  • The addition on α,β-unsaturated trifluoromethyl ketones provided an efficient preparation of enantioenriched trifluoromethylated allylic alcohols

Thesis positions available:

 

1) Asymmetric Crotylation and allylation reaction 

2) Asymmetric synthesis of novel N-N atropisomers

3) Atroposelective Heck reactions

4) Computational studies of reaction mechanisms

CONTACTS

Prof. Dr. Giorgio Bencivenni, PhD

Prof. of Organic Chemistry.
Teaching: Chimica Organica Superiore, Chimica Organica 2, Chimica Organica 1 con Laboratorio

viale del Risorgimento 4, 40136, Bologna-Italy

+390512093624

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http://www.studentidisabili.unibo.it/chi-siamo/contatti
https://twitter.com/gbbencio; https://twitter.com/LabSynthesis

Prof. Dr. Paolo Righi, PhD

Prof. of Organic Chemistry
Teaching: Chimica Organica 2, Chimica Organica Magistrale

viale del Risorgimento 4, 40136, Bologna-Italy

+39 051 20 9 3640

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Prof. Emanuela Marotta

Prof. of Organic Chemistry
Teaching: Chimica Organica 2

viale del Risorgimento 4, 40136, Bologna-Italy

+39 051 20 9 3640

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Department of Industrial Chemistry Toso Montanari