Iridium‐Catalyzed Asymmetric Hydrogenation of <i>N</i>‐Alkyl α‐Aryl Furan‐Containing Imines: an Efficient Route to Unnatural <i>N</i>‐Alkyl Arylalanines and Related Derivatives.

Mazuela, Javier; Antonsson, Thomas; Knerr, Laurent; Marsden, S. P.; Munday, Rachel H.; Johansson, Magnus J.

doi:10.1002/adsc.201801143

Cited by 15 publications

(9 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They accessed unnatural N-alkylated phenylalanine analogs via asymmetric hydrogenation of N-alkyl imine precursors in presence of an iridium catalyst. [139] A recent breakthrough in SF 5 -tagging of proteins has been reported by Huber and co-workers. They disclosed the genetic encoding of SF 5 -phenylalanine 168 via newly developed aminoacyl-tRNA synthetases that allow site-specific incorporation into protein chains with high yields.…”

Section: Pentafluorosulfanyl Group In Medicinal Chemistrymentioning

confidence: 98%

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Kordnezhadian

Zogu

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

Pentafluorosulfanyl (SF 5 )-containing compounds and corresponding analogs are a highly valuable class of fluorine-containing building blocks owing to their unique properties. The reason for that is the set of peculiar and tremendously beneficial characteristics they can impart on molecules once introduced onto them. Despite this, their application in distinct scientific fields remains modest, given the extremely harsh reaction conditions needed to access such compounds. The recent synthetic approaches via SÀ F, and CÀ SF 5 bond formation as well as the use of SF 5containing building blocks embody a "stairway-to-heaven" loophole in the synthesis of otherwise-inaccessible chemical scaffolds only a few years ago. Herein, we report and evaluate the properties of the SF 5 group and analogs, by summarizing synthetic methodologies available to access them as well as following applications in material science and medicinal chemistry since 2015.

show abstract

Section: Pentafluorosulfanyl Group In Medicinal Chemistrymentioning

confidence: 98%

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Kordnezhadian

Zogu

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Enantioselective hydrogenation [68] to rapidly identify the choice of ligand and precatalyst combination for N‐alkyl α‐aryl ketimines containing a furyl group to give the challenging N‐alkyl D‐enantiomer has been performed in high throughput (Scheme 5a). A screen of asymmetric catalysts including (Rh, Ru, Ir precursors with sulfonated diamine ligand) gave an enantiomeric ratio of 83 : 13.…”

Section: Asymmetric Hydrogenation Reactionsmentioning

confidence: 99%

Advancement in Organic Synthesis Through High Throughput Experimentation

2021

View full text Add to dashboard Cite

and cyanoarenes has also been optimized using an HTE approach. [63] Other Photochemical TransformationsNon-activated alkyl bromides were coupled with Michael acceptors in a photoredox Giese-type reaction. [64] Reaction optimization was performed by studying the effect of photocatalyst, solvent, base, and varying amounts of radical initiator (Me 3 Si) 3 SiH on product and by-product profile. Another study of conjugate addition using photocatalytic methodology was shown for the synthesis of unnatural β-alkyl α-amino acid derivatives via decarboxylative photocatalysis. [65] Photocatalysis was performed with oxime and cyanopyridine precursors (Scheme 4g) to form primary amine products. [66] Four different solvents (acetone, DCE, ACN, DMSO), nine different photocatalysts, and two reductants were used to evaluate 45 unique reactions. DMSO with diisopropylamine and Ir[dF(Me) ppy] 2 dtbbpyPF 6 gave the highest yield by UPLC, although many Scheme 4. Photocatalytic transformations in HTE.

show abstract

“…The f -binaphane ligand ( L27 ) has been also employed by Mazuela, Johansson and co-workers to achieve the enantioselective hydrogenation of N -alkyl α-aryl ketimines bearing a furyl moiety which are interesting scaffolds easily convertible into valuable chiral N -alkylated phenylalanine analogues (Scheme ). Large screening of various phosphine ligands revealed that L27 was the most efficient in AIH of this particular skeleton. Under 30 atm of H 2 , the corresponding chiral amines were obtained with moderate to good enantioselectivities and with good to excellent yields.…”

Section: Iridium-based Catalystsmentioning

confidence: 99%

Metal-Catalyzed Asymmetric Hydrogenation of C═N Bonds

et al. 2020

View full text Add to dashboard Cite

This review recaps the achievements in the field of metal-catalyzed asymmetric direct hydrogenation of nonactivated and activated imines. A summary of the reported catalytic systems with the corresponding reactivity, selectivity, and limitations are given including a discussion about the effects of some reaction conditions on the enantioselectivity of imine hydrogenation. An analysis of proposed imine hydrogenation mechanisms is discussed.

show abstract

Iridium‐Catalyzed Asymmetric Hydrogenation of N‐Alkyl α‐Aryl Furan‐Containing Imines: an Efficient Route to Unnatural N‐Alkyl Arylalanines and Related Derivatives.

Cited by 15 publications

References 63 publications

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Advancement in Organic Synthesis Through High Throughput Experimentation

Metal-Catalyzed Asymmetric Hydrogenation of C═N Bonds

Contact Info

Product

Resources

About