Asymmetric hydrogenation of trisubstituted N-acetyl enamides derived from 2-tetralones using ruthenium-SYNPHOS catalysts: a practical synthetic approach to the preparation of β3-adrenergic agonist SR58611A

Pautigny, Cyrielle; Debouit, Charlotte; Vayron, Philippe; Ayad, Tahar; Ratovelomanana‐Vidal, V.

doi:10.1016/j.tetasy.2010.03.024

Cited by 27 publications

(11 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phosphite/phosphinite‐thioether ligands L1 ‐ L8a ‐ f were prepared as previously reported [16] . Substrates S1 , [30] S2 , [12e] S3 – S4 , [30] S5 – S7 , [12g] S8 , [31] S9 – S10 , [32] S11 , [33] S12 , [32] S13 , [33] S14 , [34] S15 – S18 , [13b] S19 , [35] S20 , [13a] S21 , [36] S22 , [37] S28 , [6g] S29 , [38] S30 – S37 , [6g] S38 , [39] S39 – S43 , [22b] S44 , [40] S45 – S46 , [27j] S47 , [41] S48 , [27j] S49 , [27i] S50 [27a] were prepared following the reported procedures. 1 H, 13 C and 31 P NMR spectra were recorded using a 400 MHz spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Indene Derived Phosphorus‐Thioether Ligands for the Ir‐Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

et al. 2021

View full text Add to dashboard Cite

A family of phosphite/phosphinite‐thioether ligands have been tested in the Ir‐catalyzed asymmetric hydrogenation of a range of olefins (50 substrates in total). The presented ligands are synthesized in three steps from cheap indene and they are air‐stable solids. Their modular architecture has been crucial to maximize the catalytic performance for each type of substrate. Improving most Ir‐catalysts reported so far, this ligand family presents a broader substrate scope, covering different substitution patterns with different functional groups, ranging from unfunctionalized olefins, through olefins with poorly coordinative groups, to olefins with coordinative functional groups. α,β‐Unsaturated acyclic and cyclic esters, ketones and amides were hydrogenated in enantioselectivities ranging from 83 to 99% ee. Enantioselectivities ranging from 91 to 98% ee were also achieved for challenging substrates such as unfunctionalized 1,1′‐disubstituted olefins, functionalized tri‐ and 1,1′‐disubstituted vinyl phosphonates, and β‐cyclic enamides. The catalytic performance of the Ir‐ligand assemblies was maintained when the environmentally benign 1,2‐propylene carbonate was used as solvent.

show abstract

Section: Methodsmentioning

confidence: 99%

Indene Derived Phosphorus‐Thioether Ligands for the Ir‐Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

et al. 2021

View full text Add to dashboard Cite

show abstract

“…A similar method was also utilized by Agbossou and Ratovelomanana-Vidal for the synthesis of an atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A. Using a ruthenium complex of ( R )-MeO-BIPHEP ( L2 R ) or ( R )-SynPhos ( L25 , Ar = Ph), a cyclic enamide bearing a 7-OMe substituent was hydrogenated with up to 98% and 95% ee, respectively. , …”

Section: Synthesis Of N-substituted Chiral Cycloalkanesmentioning

confidence: 99%

Asymmetric Hydrogenation of Nonaromatic Cyclic Substrates

2016

View full text Add to dashboard Cite

Chiral cyclic structures are found in numerous natural products, pharmaceutical compounds, and important synthetic intermediates. Asymmetric hydrogenation, allowing for the preparation of these complex targets in an environmentally benign and efficient manner, has received much attention over the past few years. This review summarizes the advances in the construction of chiral heterocycles and carbocycles (including cyclic amines, ethers, alcohols, and alkanes) via the asymmetric hydrogenation of nonaromatic cyclic substrates (including prochiral cyclic imines, ketones, and alkenes) using appropriate transition-metal complexes.

show abstract

“…In 2010, we reported an efficient ruthenium‐catalyzed AH of trisubstituted enamides derived from 2‐tetralones to access 2‐aminotetralin derivatives,10 which were important structural units commonly encountered in many natural products or several drug candidates11 and were the object of intense efforts 12. The optimized reaction conditions established for N‐acetyl enamide 1a used dimeric [{RuCl(( R )‐SYNPHOS)} 2 ( μ ‐Cl) 3 ][Me 2 NH 2 ] catalyst 6 bearing the in‐house developed electron‐rich SYNPHOS7 ligand, in MeOH at 20°C under 40 bar of hydrogen pressure.…”

Section: Asymmetric Hydrogenation (Ah)mentioning

confidence: 99%

Transition‐Metal‐Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation: Sustainable Chemistry to Access Bioactive Molecules

Ayad

Phansavath

Ratovelomanana‐Vidal

2016

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Over the last few decades, the development of new and highly efficient synthetic methods to obtain chiral compounds has become an increasingly important and challenging research area in modern synthetic organic chemistry. In this account, we review recent work from our laboratory toward the synthesis of valuable chiral building blocks through transition-metal-catalyzed asymmetric hydrogenation and transfer hydrogenation of C=O, C=N and C=C bonds. Application to the synthesis of biologically relevant products is also described.

show abstract

Asymmetric hydrogenation of trisubstituted N-acetyl enamides derived from 2-tetralones using ruthenium-SYNPHOS catalysts: a practical synthetic approach to the preparation of β3-adrenergic agonist SR58611A

Cited by 27 publications

References 51 publications

Indene Derived Phosphorus‐Thioether Ligands for the Ir‐Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

Indene Derived Phosphorus‐Thioether Ligands for the Ir‐Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

Asymmetric Hydrogenation of Nonaromatic Cyclic Substrates

Transition‐Metal‐Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation: Sustainable Chemistry to Access Bioactive Molecules

Contact Info

Product

Resources

About