Gold-catalyzed enantioselective functionalization of indoles
Gold catalysis and indole chemistry are two mature and prolific fields. The gold-catalyzed functionalization of indoles has produced numerous results and paved the way for novel strategies in the building of molecular complexity. However - and curiously - though enantioselective gold catalysis is no...
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| Published in | Organic & biomolecular chemistry Vol. 18; no. 31; pp. 66 - 617 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
21.08.2020
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1477-0520 1477-0539 1477-0539 |
| DOI | 10.1039/d0ob01245a |
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| Summary: | Gold catalysis and indole chemistry are two mature and prolific fields. The gold-catalyzed functionalization of indoles has produced numerous results and paved the way for novel strategies in the building of molecular complexity. However - and curiously - though enantioselective gold catalysis is now a well-established field, it has been relatively little applied to the modification of indoles. This review highlights most of the enantioselective gold-catalyzed examples of the functionalization of indoles in order to emphasize the strengths and limitations of the method.
This review documents the potential of enantioselective gold catalysis for the functionalization of indoles. |
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| Bibliography: | Boc nitrone theme and the total synthesis of several bisindolic alkaloids. He made a first post-doctoral stay in the group of Pr Anthony G. M. Barrett at Imperial College London in the field of heterocyclic chemistry. He then joined the ICSN (Gif sur Yvette, France) for a two-year post-doc in the group of Dr Emmanuel Roulland where he developed the total synthesis of polyketide natural products. He was appointed a CNRS Chargé de Recherche in 2009 at the ICSN where he developed for few years the synthesis of nitrogen and phosphorus containing glycomimetics. He then moved to the synthesis of polycyclic chiral alkaloids using catalytic strategies, mainly focused around Au C Angélique Ferry was born in Mulhouse (France) in 1987. Angélique obtained her master's degree in 2010. She then started her PhD on the synthesis of phostone and hydroxylamine-type glycomimetics (Prof. Crich and Dr. Guinchard, ICSN). She received in 2014 the Dina Surdin PhD Award of the French Chemical Society. Then, she joined the Prof. F. Glorius group (Germany) to work on heterogeneous C-H functionalization and on N-heterocyclic carbene-stabilized metallic nanoparticles. In 2015, she became an associate professor at the University of Cergy-Pontoise. She developed metal-catalyzed functionalization of glycosides. She received, in 2018, the "women and science" award of the University of Cergy-Pontoise and a "Young Researchers" ANR funding as a project coordinator. She was awarded in 2020 the Marc Julia Prize from the Organic Chemistry Division of the French Chemical Society and won the GFG Prize 2020 by the French Glycoscience Group. nucleoside analogue of ribavirin and its prodrugs for antitumor activity in the group of Prof. Nadège Lubin-Germain at the University of Cergy-Pontoise (France). In 2019 he joined the ICSN (France) as a post-doctoral researcher to study the gold-catalyzed functionalization of indoles with Dr. Xavier Guinchard. He is currently postdoctoral researcher at the ICMMO (France), working with Dr. Guillaume Vincent in collaboration with Xavier Guinchard at ICSN. catalyzed carboamination reactions to allenes under the supervision of Dr. Xavier Guinchard. He then started his PhD in the same team to develop new approaches to chiral heterocyclic compounds using Au Pierre Milcendeau obtained his master's degree from the University Paris-Saclay in 2019. He joined the ICSN the same year as a master's student to study some Au i catalysis. (asymmetric) catalysis and the gold-catalyzed functionalization of indoles. Xavier Guinchard received in 2017 the Young Chemist Award from the French Chemical Society Organic Division. Nazarii Sabat received his PhD degree in Organic Chemistry from the Charles University and IOCB (Prague, Czech Republic) in 2017 under the supervision of Prof. Michal Hocek, where he developed novel C-H activations and cross-coupling reactions for modification of deazapurine nucleobases. From 2018 to 2019, he worked as a post-doctoral researcher on the synthesis of a new Xavier Guinchard received in 2006 a PhD degree from the University Joseph Fourier in Grenoble (France), where he developed with Dr Jean-Noël Denis methodologies around the N ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
| ISSN: | 1477-0520 1477-0539 1477-0539 |
| DOI: | 10.1039/d0ob01245a |