When Chirality Meets “Buchwald-Type” Phosphines: Synthesis and Evaluation in Frustrated Lewis Pair-, Lewis Base- and Palladium-Promoted Asymmetric Catalysis

2016 ◽  
Vol 2016 (26) ◽  
pp. 4545-4553 ◽  
Author(s):  
Mickaël J. Fer ◽  
Joséphine Cinqualbre ◽  
Julien Bortoluzzi ◽  
Matthieu Chessé ◽  
Frédéric R. Leroux ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Base ◽  
Frustrated Lewis Pair

scholarly journals Metal-free oxidative cross-coupling enabled practical synthesis of atropisomeric QUINOL and its derivatives

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Peng-Ying Jiang ◽  
Kai-Fang Fan ◽  
Shaoyu Li ◽  
Shao-Hua Xiang ◽  
Bin Tan
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Academic Research ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Industrial Applications ◽  
Lewis Base ◽  
Production Costs ◽  
Metal Free ◽  
Base Catalysts

AbstractAs an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.

Recent progress in Lewis acid-Lewis base bifunctional asymmetric catalysis

2005 ◽  
Vol 77 (12) ◽  
pp. 2047-2052 ◽  
Author(s):  
Motomu Kanai ◽  
Nobuki Kato ◽  
Eiko Ichikawa ◽  
Masakatsu Shibasaki
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acid ◽  
Recent Progress ◽  
Lewis Base ◽  
Pyridine Derivatives ◽  
Asymmetric Catalysts ◽  
Strecker Reaction

Two enantioselective cyanation reactions, the Strecker reaction of ketoimines and the Reissert reaction of pyridine derivatives, promoted by Lewis acid-Lewis base bifunctional asymmetric catalysts are described.

Developing carbon Lewis base/boron Lewis acid frustrated Lewis pair chemistry derived from conjugated dienamines

Tetrahedron ◽  
2019 ◽  
Vol 75 (5) ◽  
pp. 571-579 ◽  
Author(s):  
Jennifer Möricke ◽  
Florian Rehwinkel ◽  
Tobias Danelzik ◽  
Constantin G. Daniliuc ◽  
Birgit Wibbeling ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Lewis Base ◽  
Frustrated Lewis Pair

One-Electron Bonds in Frustrated Lewis Pair TPB Ligands: Boron Behaving as a Lewis Base

2017 ◽  
Vol 56 (24) ◽  
pp. 6788-6792 ◽  
Author(s):  
Elena Kusevska ◽  
M. Merced Montero-Campillo ◽  
Otilia Mó ◽  
Manuel Yáñez
Keyword(s):  
Lewis Base ◽  
Frustrated Lewis Pair

Gold catalyzed hydrogenations of small imines and nitriles: enhanced reactivity of Au surface toward H2via collaboration with a Lewis base

2014 ◽  
Vol 5 (3) ◽  
pp. 1082-1090 ◽  
Author(s):  
Gang Lu ◽  
Peng Zhang ◽  
Dongqing Sun ◽  
Lei Wang ◽  
Kebin Zhou ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Lewis Base ◽  
Frustrated Lewis Pair

Au (111) surface can serve as a Lewis acid to couple with a Lewis base (e.g. imine or nitrile) to form the Au-coupled FLP (frustrated Lewis pair, left) which can cleave H2, further achieving hydrogenation of small imines and nitriles.

Power of Cooperativity: Lewis Acid—Lewis Base Bifunctional Asymmetric Catalysis

ChemInform ◽  
2005 ◽  
Vol 36 (41) ◽  
Author(s):  
Motomu Kanai ◽  
Nobuki Kato ◽  
Eiko Ichikawa ◽  
Masakatsu Shibasaki
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acid ◽  
Lewis Base

Asymmetric C–Heteroatom Bond Formation

2015 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Asymmetric Catalysis ◽  
Covalent Binding ◽  
Asymmetric Hydrogenation ◽  
Lewis Base ◽  
State University ◽  
Asymmetric Allylation ◽  
Colorado State University ◽  
Asymmetric Hydrogenations ◽  
Reversible Covalent ◽  
The University

Tomislav Rovis at Colorado State University developed (Angew. Chem. Int. Ed. 2012, 51, 5904) an enantioselective catalytic cross-aza-benzoin reaction of aldehydes 1 and N-Boc imines 2. The useful α-amido ketone products 4 were configurationally stable under the reaction conditions. In the realm of asymmetric synthesis, few technologies have been as widely employed as the Ellman chiral sulfonamide auxiliary. Francisco Foubelo and Miguel Yus at the Universidad de Alicante in Spain have adapted (Chem. Commun. 2012, 48, 2543) this approach for the indium-mediated asymmetric allylation of ketimines 5, which furnished amines 6 with high diastereoselectivity. There has been vigorous research in recent years into the use of NAD(P)H surrogates, especially Hantzsch esters, for biomimetic asymmetric hydrogenations. Yong-Gui Zhou at the Chinese Academy of Sciences showed (J. Am. Chem. Soc. 2012, 134, 2442) that 9,10-dihydrophenanthridine (10) can also serve as an effective “H2” donor for the asymmetric hydrogenation of imines, including 7. Notably, 10 is used catalytically, with regeneration occurring under mild conditions via Ru(II)-based hydrogenation of the phenanthridine 11. A unique approach for asymmetric catalysis has been developed (Nature Chem. 2012, 4, 473) by Takashi Ooi at Nagoya University, who found that ion-paired complexes 14 could serve as effective chiral ligands in the Pd(II)-catalyzed allylation of α-nitrocarboxylates 12. The resulting products 13 are easily reduced to furnish α-amino acid derivatives. Another novel catalytic platform has been employed (J. Am. Chem. Soc. 2012, 134, 7321) for the chiral resolution of 1,2-diols 15 by Kian L. Tan at Boston College. Using the concept of reversible covalent binding, the catalyst 16 was found to selectively silylate a secondary hydroxyl over a primary one, thus leading to the enantioenriched products 17 and 18. Scott E. Denmark at the University of Illinois has applied (Angew. Chem. Int. Ed. 2012, 51, 3236) his chiral Lewis base strategy to the enantioselective vinylogous aldol reaction of N-silyl vinylketene imines 19 to produce γ-hydroxy-α,β-unsaturated nitriles 22. For the preparation of enantioenriched homopropargylic alcohols 25, the asymmetric addition of allenyl metal nucleophiles (e.g., 24) to aldehydes 23 provides a straightforward approach.

Recent Progress in Lewis Acid—Lewis Base Bifunctional Asymmetric Catalysis

ChemInform ◽  
2006 ◽  
Vol 37 (24) ◽  
Author(s):  
Motomu Kanai ◽  
Nobuki Kato ◽  
Eiko Ichikawa ◽  
Masakatsu Shibasaki
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acid ◽  
Recent Progress ◽  
Lewis Base

One-Electron Bonds in Frustrated Lewis Pair TPB Ligands: Boron Behaving as a Lewis Base

2017 ◽  
Vol 129 (24) ◽  
pp. 6892-6896 ◽  
Author(s):  
Elena Kusevska ◽  
M. Merced Montero-Campillo ◽  
Otilia Mó ◽  
Manuel Yáñez
Keyword(s):  
Lewis Base ◽  
Frustrated Lewis Pair
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