Iron‐Catalysed Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids to Access Cyclic Amines

Wei, Duo; Netkaew, Chakkrit; Carré, Victor; Darcel, Christophe

doi:10.1002/cssc.201900519

Cited by 19 publications

(9 citation statements)

References 80 publications

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“…Recently, we have developed an iron‐catalysed one‐pot preparation of N ‐substituted cyclic amines via reductive amination of carbonyl derivatives with ω ‐amino fatty acids under hydrosilylation conditions [14] . During this study, we identified that the first step of the synthesis leading to the lactams did not require iron catalyst.…”

Section: Figurementioning

confidence: 99%

Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids under Hydrosilylation Conditions

Tongdee

Wei

et al. 2021

Eur J Org Chem

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An efficient method for the preparation of lactams from ω‐amino fatty acids under hydrosilylation is described. A variety of lactams such as pyrrolidinones, piperidinones and 2‐azepanones were selectively synthesised in moderate to excellent yields (29 examples, up to 95 % isolated yields) with a good functional group tolerance. Notably, no metallic based catalyst was required to perform this transformation.

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Section: Figurementioning

confidence: 99%

Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids under Hydrosilylation Conditions

Tongdee

Wei

et al. 2021

Eur J Org Chem

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“…The silylamine intermediate was generated, and piperidinone was also formed through intramolecular transamidation. N‐substituted cyclic amines were formed under hydrosilylation conditions catalyzed by the Fe catalyst [18] . In the same year, based on the similar Fe‐catalyzed reductive amination system, Darcel and co‐workers reported a highly efficient synthesis method for N‐substituted pyrrolidinones and pyrrolidines starting from levulinic acid esters and a variety of amines (Scheme 4G).…”

Section: Earth‐abundant Transition Metalsmentioning

confidence: 99%

Earth‐abundant Metal‐catalyzed Reductive Amination: Recent Advances and Prospect for Future Catalysis

Liu

Song

2021

Chemistry An Asian Journal

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Nitrogen‐containing compounds, as an important class of chemicals, have been used widely in pharmaceuticals, materials synthesis. Transition metal‐catalyzed reductive amination of an aldehyde or a ketone with ammonia or an amine has been proved to be an efficient and practical method for the preparation of nitrogen‐containing compounds in academia and industry for a century. Given the above, several effective methods using transition metals have been developed in recent years. Noble transition metals like Pd, Pt, and Au‐based catalysts have been predominately used in reductive amination. Because of their high prices, strict official regulations of residues in pharmaceuticals, and deleterious effects on the biological system, their industrial applications are severely hampered. With the increasing sustainable and environmental problems, the Earth‐abundant transition metals including Ti, Fe, Co, Ni, and Zr have also been investigated for the reductive amination reaction and showed great potential to the advancement of sustainable and cost‐effective reductive amination processes. This critical review will mainly summarize the work using Earth‐abundant metals. The effects of different transition metals used in catalytic reduction amination were discussed and compared, and some suggestions were given. The last section highlights the catalytic activities of bi‐ and tri‐metallic catalysts. Indeed, this latter family is very promising and simultaneously benefits from increased stability, and selectivity, compared to monometallic NPs, due to synergistic substrate activation. Few comprehensive reviews focusing on Earth‐abundant transition metals catalyst has been published since 1948, although several authors reported some summaries dealing with one or the other part of this aspect. It is hoped that this critical review will inspire researchers to develop new efficient and selective earth‐abundant metal catalysts for highly, environmentally sustainable reductive amination methods, as well as improve the pharmaceutical industry and related chemical synthesis company traditional method with the utilization of the green method widely.

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“…Darcel's group developed a reductive amination of carbonyl derivatives 193 with ω ‐amino fatty acids 194 catalyzed by an iron complex Fe(CO) 4 (IMes) [IMes=1,3‐bis(2,4,6‐trimethylphenyl)imidazol‐2‐ylidene] 196 (Scheme 29). [46] N ‐substituted cyclic amines (including pyrrolidines, piperidines and azepanes) were selectively prepared in moderate to excellent yields with a high functional group tolerance.…”

Section: Iron‐catalyzed Synthesis Of Pyrrolidinesmentioning

confidence: 99%

Iron‐Catalyzed Synthesis of Pyrrole Derivatives and Related Five‐Membered Azacycles

Wang

Zhang

et al. 2021

Eur J Org Chem

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Pyrrole derivatives and their related five‐membered azacycles are a class of important five‐membered aromatic nitrogen heterocyclic compounds, and their synthesis attracted much the attention of organic chemists. Iron catalysis has been widely used in various organic transformations owing to their excellent catalytic activity, environmentally benign character, easy accessibility and low price. Over the past decades, a variety of facile and effective syntheses of pyrrole derivatives and related five‐membered azacycles based on iron catalysis has been reported. In this Minireview, the development of the iron‐catalyzed synthesis of pyrrole derivatives and their related five membered azacycles is reported in a comprehensive way, covering the literature up to March 2021.

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Iron‐Catalysed Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids to Access Cyclic Amines

Cited by 19 publications

References 80 publications

Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids under Hydrosilylation Conditions

Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω‐Amino Fatty Acids under Hydrosilylation Conditions

Earth‐abundant Metal‐catalyzed Reductive Amination: Recent Advances and Prospect for Future Catalysis

Iron‐Catalyzed Synthesis of Pyrrole Derivatives and Related Five‐Membered Azacycles

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