Anne Harrison-Marchand
University of Rouen
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Featured researches published by Anne Harrison-Marchand.
Chemical Reviews | 2013
Anne Harrison-Marchand; Florence Mongin
Organometallic Aggregates. 1. Structural Data Anne Harrison-Marchand*,† and Florence Mongin*,‡ †Laboratoire COBRA de l′Universite ́ de Rouen, INSA de Rouen, CNRS, UMR 6014 & FR 3038, IRCOF, Rue Tesnier̀e, 76821 Mont St Aignan Ced́ex, France ‡Équipe Chimie et Photonique Molećulaires, Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Universite ́ de Rennes 1, Bat̂iment 10A, case 1003, Avenue du Geńeŕal Leclerc, 35042 Rennes Ced́ex, France
Chemical Communications | 2011
Baptiste Lecachey; Catherine Fressigné; Hassan Oulyadi; Anne Harrison-Marchand; Jacques Maddaluno
A substoichiometric enantioselective version of the extremely fast nucleophilic addition of Alk-Li to RCHO is made possible thanks to a thorough analysis of the aggregation phenomena involved in the reaction: calculated quantities of LiCl must be added to the medium at the right time to keep the catalytic cycle running.
Tetrahedron | 2002
Karine Flinois; Yi Yuan; Christopher Bastide; Anne Harrison-Marchand; Jacques Maddaluno
Non-covalent aggregates of highly polar entities assemble, on a temporary basis, a chiral moiety to a reagent. Attempts to take advantage of this phenomenon with chiral 3-aminopyrrolidine (3-AP) lithium amides are described. The enantioselective protonation of a complex involving these amides and the lithium enolate of 2-methyltetralone by an achiral proton source gives products in which the ee does not exceed 40%. The same class of chiral amides is then applied to the asymmetric nucleophilic alkylation of aldehydes using alkyllithiums and phenyllithium. In this case, a mixed aggregate made up of the lithium amide and the alkyllithium, a structure that has been detailed previously in comparable situations, seems to be directly involved in the reaction. Thus, higher asymmetric inductions are obtained, affording the alkylation products in ee of up to 70%.
Pure and Applied Chemistry | 2006
Anne Harrison-Marchand; Jean-Yves Valnot; Aline Corruble; Nicolas Duguet; Hassan Oulyadi; Stéphanie Desjardins; Catherine Fressigné; Jacques Maddaluno
An overview of the role of 3-aminopyrrolidine lithium amides (3-APLis) as chiral ligands for alkyllithiums (AlkLis) 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 AlkLis 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.
Chemistry: A European Journal | 2016
Fatima Rebih; Manuel Andreini; Aurélien Moncomble; Anne Harrison-Marchand; Jacques Maddaluno; Muriel Durandetti
A novel Ni(0) -catalyzed carboxylation of aryl tosylates with carbon dioxide has been achieved under moderate temperatures and atmospheric pressure. In this procedure, the active Ni(0) species is generated in situ by simply mixing the Ni(0) precatalyst [NiBr2 (bipy)] with an excess of manganese metal. This approach requires neither a glove-box nor the tedious preparation of sophisticated intermediate organometallic derivatives. This mild, convenient, and user-friendly process is successfully applied to the valorization of carbon dioxide and the synthesis of versatile reactants with broad tolerance of substituents.
New Journal of Chemistry | 2012
Anne Harrison-Marchand; Hélène Gérard; Jacques Maddaluno
Organolithium reagents in solution are known to adopt oligomeric structures that are highly sensitive to the presence and nature of additives. In particular, the addition of lithium halides, chalcogenides or pnictogenides leads, in many cases, to well-defined complexes having the effect of decreasing the degree of aggregation of the original oligomer and often increasing the reactivity of the lithiated species itself. Incorporating a stereogenic element through the additive may allow the resulting complexes to be employed in stereochemically controlled reactions. In this context, two strategies can be applied that are the usual picture of a single metal in interaction with σ-donor (non-metalated) ligand(s) e.g. spartein, or, the possibility for the main group organolithium to be associated with another chiral lithiated partner forming organo(-bi-)metallic entities in which nucleophilicity and asymmetry are coupled. To date, engaging lithio reactants in the very classical enantioselective nucleophilic addition process with aldehydes remains a challenge due to the high intrinsic reactivity of the two partners. Nevertheless, taking advantage of a thorough understanding of the aggregation phenomena between the lithiated dipolar entities all along the catalytic cycle allows the fine-tuning of a substoichiometric enantioselective hydroxyalkylation of an aldehyde by an alkyllithium. We show the application of such a strategy to an example described recently.
Archive | 2014
Anne Harrison-Marchand; Nicolas Duguet; Gabriella Barozzino-Consiglio; Hassan Oulyadi; Jacques Maddaluno
This review summarizes detailed investigations on the enantioselective nucleophilic addition of organolithiums onto prochiral electrophilic substrates, one of the simplest reaction meant to create a C–C bond, using dipolar bimetallic systems. Interestingly, these very popular and useful chemical transformations, even if taught at the undergraduate level, have remained underdeveloped when it comes to their enantioselective versions. The systems we present consist of a nucleophilic organolithium (NuLi) in strong dipolar interaction with a second lithiated entity bearing the source of asymmetry, i.e., a chiral lithium amide (CLA) derived from a 3-aminopyrrolidine (3APLi). Several 1:1 3APLi/NuLi noncovalent mixed aggregates are described and their relevance to the enantioselective process is discussed. Since the Curtin–Hammett principle forbids to correlate the complexes to the final ees of the products, we have run complementary experiments of which results led us to propose the participation of an ephemeral, but more reactive, triptych aggregate.
Tetrahedron | 2005
Yi Yuan; Stéphanie Desjardins; Anne Harrison-Marchand; Hassan Oulyadi; Catherine Fressigné; Claude Giessner-Prettre; Jacques Maddaluno
Chemical Communications | 2014
Ghanem Hamdoun; Muriel Sebban; E. Cossoul; Anne Harrison-Marchand; Jacques Maddaluno; Hassan Oulyadi
Tetrahedron | 2004
Anne Harrison-Marchand; Sylvain Collet; André Guingant; Jean-Paul Pradère; Loı̈c Toupet