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Helical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C-C Bond-Forming Reactions

hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorBECART, Diane
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorDIEMER, Vincent
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorSALAUN, Arnaud
dc.contributor.authorOIARBIDE, Mikel
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorNELLI, Yella Reddy
hal.structure.identifierInstitut Européen de Chimie et de Biologie
dc.contributor.authorKAUFFMANN, Brice
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorFISCHER DUROLA, Lucile
dc.contributor.authorPALOMO, Claudio
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorGUICHARD, Gilles
IDREF: 084339268
dc.date.accessioned2020-07-09T14:17:15Z
dc.date.available2020-07-09T14:17:15Z
dc.date.issued2017-09
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/10363
dc.description.abstractEnSubstantial progress has been made toward the development of metal-free catalysts of enantioselective transformations, yet the discovery of organic catalysts effective at low catalyst loadings remains a major challenge. Here we report a novel synergistic catalyst combination system consisting of a peptide-inspired chiral helical (thio)urea oligomer and a simple tertiary amine that is able to promote the Michael reaction between enolizable carbonyl compounds and nitroolefins with excellent enantioselectivities at exceptionally low (1/10 000) chiral catalyst/substrate molar ratios. In addition to high selectivity, which correlates strongly with helix folding, the system we report here is also highly amenable to optimization, as each of its components can be fine-tuned separately to increase reaction rates and/or selectivities. The predictability of the foldamer secondary structure coupled to the high level of control over the primary sequence results in a system with significant potential for future catalyst design.
dc.title.enHelical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C-C Bond-Forming Reactions
dc.typeArticle de revue
dc.identifier.doi10.1021/jacs.7b05802
dc.subject.halChimie/Matériaux
bordeaux.journalJournal of the American Chemical Society
bordeaux.page12524-12532
bordeaux.volume139
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248*
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN, UMR 5248)
bordeaux.issue36
bordeaux.institutionUniversité de Bordeaux
bordeaux.institutionBordeaux INP
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.date=2017-09&rft.volume=139&rft.issue=36&rft.spage=12524-12532&rft.epage=12524-12532&rft.au=BECART,%20Diane&DIEMER,%20Vincent&SALAUN,%20Arnaud&OIARBIDE,%20Mikel&NELLI,%20Yella%20Reddy&rft.genre=article


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