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  Strong and Confined Acid Catalysts Impart Stereocontrol onto the Non-Classical 2-Norbornyl Cation

Properzi, R., Kaib, P. S. J., Leutzsch, M., Pupo, G., Mitra, R., De, C. K., et al. (2019). Strong and Confined Acid Catalysts Impart Stereocontrol onto the Non-Classical 2-Norbornyl Cation. doi:10.26434/chemrxiv.10887914.v1.

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Properzi, Roberta1, Autor           
Kaib, Philip S. J.1, Autor           
Leutzsch, Markus2, Autor           
Pupo, Gabriele1, Autor           
Mitra, Raja1, Autor           
De, Chandra Kanta1, Autor           
Schreiner, Peter R.3, Autor
List, Benjamin1, Autor           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              
3Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, D-35392 Giessen, Germany, ou_persistent22              

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Schlagwörter: 2-norbornyl; asymmetric catalysis; ACDC; carbonium ions; non-classical carbocation
 Zusammenfassung: Utilizing carbocationic intermediates
in asymmetric transformations is a challenge for catalysis. While recent studies have provided promising approaches to systems proceeding through classical, trivalent carbenium ions, we were particularly intrigued by the possibility of imparting stereochemical control onto the 2-norbornyl cation, a small, fully aliphatic and positively-charged hydrocarbon that is known to adopt a non-classical structure. We now show that strong and confined imidodiphosphorimidate (IDPi) catalysts
are competent acids for carrying out a
n asymmetric stereoablative C–C bond forming reaction, utilizing racemic exo- or
endo-norbornyl derivatives to exclusively
obtain the highly enantioenriched
exo-product. In addition, structurally-different substrates can be converted to the same product with remarkable enantioselectivities
by leveraging the reactivity of a variety of functional groups. Mechanistic and kinetic studies suggest that all employed substrates proceed through a common cationic intermediate.

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Sprache(n): eng - English
 Datum: 2019-11-232019-11-23
 Publikationsstatus: Online veröffentlicht
 Seiten: 14
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Keine Begutachtung
 Identifikatoren: DOI: 10.26434/chemrxiv.10887914.v1
 Art des Abschluß: -

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Titel: ChemRxiv
Genre der Quelle: Kommentar
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Affiliations:
Ort, Verlag, Ausgabe: American Chemical Society (ACS), Chinese Chemical Society, Chemical Society of Japan, German Chemical Society (GDCh), Royal Society of Chemistry
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