Asymmetric synthesis and methodologies by using both metal (particularly copper reagents) and nonmetallic catalysts (organocatalysis); Chiral bases and chiral protonation reagents; Development of new reactions and new methodologies for organic synthesis; Design of new chiral ligands, particularly the ones derived from C2 symmetrical diamines and diols; Application to the synthesis of natural products.
 

• Asymmetric synthesis in a wide sense.
  

• Catalytic organocopper chemistry from the asymmetric point of view.
  

• Chiral bases and chiral protonation reagents.
  

• Development of new reactions and new methodologies for organic synthesis.
  

• New Organocatalysed reactions and organocatalysts.
  

• Design of new chiral ligands, particularly the ones derived from C2 symmetrical diamines and diols.
  

• Application to the synthesis of natural products.
  

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Organocatalysis

Design of new powerful catalysts:

iPBP Michael addition of aldehydes and ketones to nitroolefins	Aminal-Pyrrolidines Michael addition to vinyl sulfones, nitrodienes. Chlorination, amination and iminium catalysis.

Application of new nucleophiles / electrophiles for the synthesis of valuable synthons:

Nucleophiles:
Electrophiles:

 

Combination of organometallic and organocatalysis for the generation of high molecular complexity:
 

Au-Organocatalysis:
Cu-Organocatalysis:
Ir-Organocatalysis:

 

Related publications: 

Catalyst design: Eur. J. Org. Chem. 2010, 927-936 • Chem. Eur. J. 2008, 14, 7504-7507 • Adv. Synth. Cat. 2004, 346, 1147-1168 • Org. Lett. 2002, 4, 3611-3614.

New nucleophiles / electrophiles: Chem. Commun. 2010, 46, 4085-4087 • Tetrahedron: Asymmetry 2010, 21, 1666-1673 • Chem. Eur. J. 2009, 15, 11109-11113 • Org. Lett. 2008, 10, 4557-4560 • Chem. Commun. 2008, 4694-4696 • Org. Lett. 2007, 9, 3749-3752 • Org. Lett. 2005, 7, 4361-4364 • Org. Lett. 2003, 5, 2559-2561.

Metal-organocatalysis combination: Adv. Synth. Catal. 2010, 352,1856-1860 • Adv. Synth. Catal. 2010, 352,667-695 • Angew. Chem. Int. Ed. 2009, 48, 8923-8926.

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Ring opening of O or N bridge

• Ring Opening of meso Epoxides:

 

• Ring Opening of Cyclic Vinyl Epoxides:

 

• Ring Opening of meso bicyclic hydrazines:

 

• Ring Opening of Oxabenzonorbornadienes:

 

• Ring Opening Cyclic Alkenyl Cyclopropane Malonates:

 

Related Publications:

Org. Lett. 2010, 12, 576-579 • Synlett 2010, 317-320 • Eur. J. Org. Chem. 2009, 4949-4955 • Synthesis 2009, 2101-2112 • Tetrahedron Lett. 2009, 50, 3474-3477 • Synlett 2008, 12, 1797-1800 • Synlett 2007, 435-438 • Org. Lett. 2006, 8, 3581-3584 • Eur. J. Org. Chem. 2005, 1354-1366 • In Methodologies in Asymmetric Catalysis, S. V. Malhotra, Ed.; ACS Symposium Series, Volume 880, Washington, 2004, 43-59 • Tetrahedron: Asymmetry 2004, 15, 1531-1536 • Eur. J. Org. Chem. 2004, 2151-2159 • Tetrahedron: Asymmetry 2004, 15, 1069-1072 • J. Chem. Soc., Perkin Trans. 1 2000, 3354-3355 • J. Chem. Soc., Perkin Trans. 1 2000, 3352-3353 • Synlett 1998, 1165-1167.

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Asymmetric Conjugate Addition

• Creation of quaternary stereogenic centres:

Till the first publication of creation of quaternary stereogenic centres via copper catalyzed conjugate asymmetric addition (ACIE, 2005, 1376-1378) great research efforts have been done to extend the scope of nucleophiles and substrates in this area.

 

• Scope of nucleophiles used for Cu-catalyzed ACA:

Alkyl nucleophiles:

M. d'Augustin, L. Palais, A. Alexakis, 
Angew Chem. Int. Ed. 2005, 44, 1376-1378.

 

D. Martin, S. Kehrli, M. d'Augustin, H. Clavier, M. Mauduit, A. Alexakis, 
J. Am. Chem. Soc. 2006, 128, 8416-8417.

 

H. Hénon, M. Mauduit, A. Alexakis, 
Angew. Chem. Int. Ed. 2008, 47, 9122-9124.

 

Alkenyl nucleophiles:

D. Müller, C. Hawner, M. Tissot, L. Palais, A. Alexakis, 
Synlett 2010, 1694-1698.

 

Aryl nucleophiles:

C. Hawner, K. Li, V. Cirriez, A. Alexakis, 
Angew. Chem. Int. Ed. 2008, 47, 8211-8214.

C. Hawner, D. Müller, L. Gremaud, A. W. Felouat, S. Woodward, A. Alexakis, 
Angew Chem. Int. Ed. 2010, 122, 7769-7772.

• "New" substrates for the copper catalyzed ACA:

New original and challenging substrates have also been applied in copper catalysis.

L. Palais, L. Babel, A. Quintard, S. Belot, A. Alexakis, 
Org. Lett. 2010, 12, 1988-1991.

 

M. Tissot, D. Müller, S. Belot, A. Alexakis, 
Org. Lett. 2010, 12, 2770-2773.

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Asymmetric Br-Li Exchange

• Design of new ligand:

 

• Brome-Lithium exchange catalyzed by ether diamines or diether derivatives:

 

Related publications:  Tetrahedron: Asymmetry 2009, 20, 1004-1007 • Adv. Synth. Catal. 2010, 352, 2611-2620.