Chimie Peptidomimétique Photochimie et Procédés Alternatifs
Responsable : Marie-Christine Scherrmann
Mail : marie-christine.scherrmann@universite-paris-saclay.fr
Tél. : +33 1 69 15 72 56
Organocatalytic transformations of cyclobutanones
Cyclobutanones are a useful family of small ring building blocks for organic synthesis. Part of the organocatalysis programme carried out in the CP3A group is focused on new transformations of cyclobutanones to access more complex intermediates in a stereoselective fashion. Using prochiral 3-substituted cyclobutanones as substrates, desymmetrizing transformations are performed stereoselectively, sometimes accompanied by ring opening processes. With racemic 2-hydroxycyclobutanone as the starting material, aldol or Amadori-Heyns-type reactions are conducted with controlled selectivities, while recently an Brønsted acid catalysed tandem reaction with anilines was discovered, leading directly to tryptamine derivatives in an unprecedented manner.
This work constitutes a long-standing collaboration with the research group of Profs P. P Piras, A. Frongia and Dr F. Secci of the University of Cagliari (Italy). Dr Secci is a visiting professor hosted in our group in Autumn 2017.
Overview of results
List of publications
Unexpected formation of optically active 4-substituted 5-hydroxy-γ-lactams by organocatalyzed reaction of 3-substituted cyclobutanones with nitrosobenzene. F. CAPITTA, A. FRONGIA, J. OLLIVIER, P. P. PIRAS, F. SECCI, Synlett, 2011, 89-93.
The first organocatalysed direct aldol reaction of 2-hydroxycyclobutanone. D. J. AITKEN, F. CAPITTA, A. FRONGIA, D. GORI, R. GUILLOT, J. OLLIVIER, P. P. PIRAS, F. SECCI, M. SPIGA, Synlett, 2011, 712-716.
Solvent-free stereoselective organocatalyzed aldol reaction of 2-hydroxycyclobutanone. D. J. AITKEN, F. CAPITTA, A. FRONGIA, J. OLLIVIER, P. P. PIRAS, F. SECCI, Synlett, 2012, 727-730.
Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones. D. J. AITKEN, A. M. BERNARD, F. CAPITTA, A. FRONGIA, R. GUILLOT, J. OLLIVIER, P. P. PIRAS, F. SECCI, M. SPIGA, Org. Biomol. Chem., 2012, 10, 5045-5048.
Catalytic enantioselective synthesis of α-arylamino cyclobutanones. D. J. AITKEN, P. CABONI, H. EIJSBERG, A FRONGIA, R. GUILLOT, J. OLLIVIER, P. P. PIRAS, F. SECCI, Adv. Synth. Catal., 2014, 356, 941-945.
Enantioselective organocatalyzed desymmetrization of 3-substituted cyclobutanones via Michael addition to nitroalkenes. F. CAPITTA, A. FRONGIA, J. OLLIVIER, D. J. AITKEN, F. SECCI, P. P. PIRAS, R. GUILLOT, Synlett, 2015, 26, 123-126.
Catalytic enantioselective synthesis of α-benzylamino cyclobutanones. N. MELIS, L. GHISU, R. GUILLOT, P. CABONI, F. SECCI, D. J. AITKEN, A. FRONGIA, Eur. J. Org. Chem., 2015, 4358-4366.
Synthesis of functionalized tryptamines by Brønsted acid catalyzed cascade reactions. N. MELIS, F. SECCI, T. BODDAERT, D. J. AITKEN, A. FRONGIA, Chem. Commun., 2015, 51, 15272-15275.
Deracemizing organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with β-nitrostyrenes. A. LURIDIANA, A. FRONGIA, D. J. AITKEN, R. GUILLOT, G. SARAIS, F. SECCI, Org. Biomol. Chem., 2016, 14, 3394-3403.