New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine

Cobley, Christopher J.; Evans, George; Fanjul, Tamara; Simmonds, Shaun; Woods, Amy L.

doi:10.1016/j.tetlet.2016.01.060

Cited by 12 publications

(10 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…371−374 Overall, these protocols allowed an efficient route to the asymmetric synthesis of 2-aminotetralines and 3-aminochromanes, key structural units in many biologically active agents such as rotigotine, terutroban, and nepicastat (Figure 6). 375,376 The AH of tetrasubstituted endocyclic enamides 29 has been a focus of great attention over the last years. The resulting chiral cyclic amines with a substitution at the 2-position are important motifs in many bioactive molecules and drugs (Figure 7).…”

Section: Endocyclic N-acyl Enamidesmentioning

confidence: 99%

“… , The same group further extended this methodology using other modular ligands. − Overall, these protocols allowed an efficient route to the asymmetric synthesis of 2-aminotetralines and 3-aminochromanes, key structural units in many biologically active agents such as rotigotine, terutroban, and nepicastat (Figure ). , …”

Section: Asymmetric Hydrogenation Of Enamidesmentioning

confidence: 99%

See 1 more Smart Citation

Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation

2021

View full text Add to dashboard Cite

Chiral amines are key structural motifs present in a wide variety of natural products, drugs, and other biologically active compounds. During the past decade, significant advances have been made with respect to the enantioselective synthesis of chiral amines, many of them based on catalytic asymmetric hydrogenation (AH). The present review covers the use of AH in the synthesis of chiral amines bearing a stereogenic center either in the α, β, or γ position with respect to the nitrogen atom, reported from 2010 to 2020. Therefore, we provide an overview of the recent advances in the AH of imines, enamides, enamines, allyl amines, and N-heteroaromatic compounds.

show abstract

Section: Endocyclic N-acyl Enamidesmentioning

confidence: 99%

Section: Asymmetric Hydrogenation Of Enamidesmentioning

confidence: 99%

Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation

2021

View full text Add to dashboard Cite

show abstract

“…The drawback of this approach is loss of 50% undesired isomer during the resolution step. More recently asymmetric syntheses using a catalyst such as [RuCl 2 ( R )-BINAP)] 2 ·NEt 3 or enzymes have been reported. , …”

Section: Dopamine Agonists and Their Synthesismentioning

confidence: 99%

Parkinson’s Disease: Advances in Treatment and the Syntheses of Various Classes of Pharmaceutical Drug Substances

Hill,

Huters,

Towne

et al. 2023

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…Transition metal catalysis has also been employed successfully through the hydrogenation of cyclic 2-enamides (Scheme 1). [17][18][19][20][21] However, limitations are also associated with these approaches, including sensitivity to moisture and the use of expensive non-commercial chiral ligands. [22,23] Other relevant, yet less effective approaches towards the synthesis of these moieties include the asymmetric aziridination of dihydronaphthalenes, [24] the organocatalytic reductive amination of 2-tetralones, [25] and the radical cyclisation of substituted benzenes with l-serine derivatives.…”

Section: Chiralaminesoccupyaprominentroleduetotheirsyntheticmentioning

confidence: 99%

Synthesis of Pharmaceutically Relevant 2‐Aminotetralin and 3‐Aminochroman Derivatives via Enzymatic Reductive Amination

et al. 2021

View full text Add to dashboard Cite

2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for > 15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT. We also present a convergent chemo-enzymatic total synthesis of the Parkinsons disease therapy Rotigotine in 63 % overall yield and 92 % ee.

show abstract

New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine

Cited by 12 publications

References 36 publications

Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation

Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation

Parkinson’s Disease: Advances in Treatment and the Syntheses of Various Classes of Pharmaceutical Drug Substances

Synthesis of Pharmaceutically Relevant 2‐Aminotetralin and 3‐Aminochroman Derivatives via Enzymatic Reductive Amination

Contact Info

Product

Resources

About