3-Aminopyrrolidine Lithium Amides as Chiral Ligands for Alkyllithium Derivatives: Synthesis, NMR Analysis, and Computational Study of Their Mixed Aggregates

ChemInform ◽  
2006 ◽  
Vol 37 (33) ◽  
Author(s):  
Anne Harrison-Marchand ◽  
Jean-Yves Valnot ◽  
Aline Corruble ◽  
Nicolas Duguet ◽  
Hassan Oulyadi ◽  
...  
Keyword(s):  
Computational Study ◽  
Chiral Ligands ◽  
Nmr Analysis ◽  
Lithium Amides ◽  
Mixed Aggregates

3-Aminopyrrolidine lithium amides as chiral ligands for alkyllithium derivatives: Synthesis, NMR analysis, and computational study of their mixed aggregates

2006 ◽  
Vol 78 (2) ◽  
pp. 321-331 ◽  
Author(s):  
Anne Harrison-Marchand ◽  
Jean-Yves Valnot ◽  
Aline Corruble ◽  
Nicolas Duguet ◽  
Hassan Oulyadi ◽  
...  
Keyword(s):  
Computational Study ◽  
Ligand Design ◽  
Model Reaction ◽  
Chiral Ligands ◽  
Nmr Analysis ◽  
Simplified Models ◽  
Lithium Amides ◽  
Mixed Aggregates

An overview of the role of 3-aminopyrrolidine lithium amides (3-APLi's) as chiral ligands for alkyllithiums (AlkLi's) is presented. Synthetic developments as well as NMR characterizations and computational interpretations have been simultaneously and complementarily conducted to improve the ligand design for a model reaction that is the condensation of AlkLi's on o-tolualdehyde, for which enantiomeric excesses up to 80 % were obtained. This study describes the whole chain going from the synthesis of the chiral 3-aminopyrrolidines (3-APs) (18 different 3-APs synthesized) to the characterization of the noncovalent mixed aggregates resulting from the interaction between the organolithium partners (3-APLi:AlkLi). Finally, the docking of the aldehyde on one lithium of the aggregate was analyzed by theoretical means on simplified models, in an attempt to understand the structure of the fully loaded pretransition complexes.

Ab initio theoretical study of 3-aminopyrrolidines lithium amides as chiral ligands for butyllithium

1997 ◽  
Vol 549 (1-2) ◽  
pp. 81-88 ◽  
Author(s):  
Catherine Fressigné ◽  
Aline Corruble ◽  
Jean-Yves Valnot ◽  
Jacques Maddaluno ◽  
Claude Giessner-Prettre
Keyword(s):  
Ab Initio ◽  
Theoretical Study ◽  
Chiral Ligands ◽  
Lithium Amides

Enantioselective Alkynylation of Aldehydes by Mixed Aggregates of 3-Aminopyrrolidine Lithium Amides and Lithium Acetylides

2015 ◽  
Vol 34 (18) ◽  
pp. 4441-4450 ◽  
Author(s):  
Gabriella Barozzino-Consiglio ◽  
Yi Yuan ◽  
Catherine Fressigné ◽  
Anne Harrison-Marchand ◽  
Hassan Oulyadi ◽  
...  
Keyword(s):  
Lithium Amides ◽  
Mixed Aggregates

Heterocyclic Lithium Amides as Chiral Ligands for an Enantioselective Hydroxyalkylation withn-BuLi

2008 ◽  
Vol 73 (14) ◽  
pp. 5397-5409 ◽  
Author(s):  
Nicolas Duguet ◽  
Sylvain M. Petit ◽  
Philippe Marchand ◽  
Anne Harrison-Marchand ◽  
Jacques Maddaluno
Keyword(s):  
Chiral Ligands ◽  
Lithium Amides

A Computational Study of Mixed Aggregates of Chloromethyllithium with Lithium Dialkylamides

2005 ◽  
Vol 70 (21) ◽  
pp. 8298-8302 ◽  
Author(s):  
Lawrence M. Pratt ◽  
Lý Thi Lê ◽  
Thanh N. Truong
Keyword(s):  
Computational Study ◽  
Mixed Aggregates

A Computational Study of Lithium Enolate Mixed Aggregates

2003 ◽  
Vol 68 (7) ◽  
pp. 2830-2838 ◽  
Author(s):  
Lawrence M. Pratt ◽  
Andrew Streitwieser
Keyword(s):  
Computational Study ◽  
Lithium Enolate ◽  
Mixed Aggregates

Solvent effects on the mixed aggregates of chiral 3-aminopyrrolidine lithium amides and alkyllithiums

Tetrahedron ◽  
2005 ◽  
Vol 61 (13) ◽  
pp. 3325-3334 ◽  
Author(s):  
Yi Yuan ◽  
Stéphanie Desjardins ◽  
Anne Harrison-Marchand ◽  
Hassan Oulyadi ◽  
Catherine Fressigné ◽  
...  
Keyword(s):  
Solvent Effects ◽  
Lithium Amides ◽  
Mixed Aggregates

ChemInform Abstract: Enantioselective Protonation and Alkylation of Non-covalent Mixed Aggregates of Chiral 3-Aminopyrrolidine Lithium Amides.

ChemInform ◽  
2010 ◽  
Vol 33 (41) ◽  
pp. no-no
Author(s):  
Karine Flinois ◽  
Yi Yuan ◽  
Christopher Bastide ◽  
Anne Harrison-Marchand ◽  
Jacques Maddaluno
Keyword(s):  
Lithium Amides ◽  
Mixed Aggregates
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