Recent advances in the synthesis of α-amino ketones

Due to the importance of the amino ketone motif in synthetic and medicinal chemistry, the number of protocols developed in recent years has considerably increased. This review serves to collate and critically evaluate novel methodologies published since 2011 towards this high value synthon. The chap...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 3; pp. 498 - 513
Main Authors Allen, Lewis A. T, Raclea, Robert-Cristian, Natho, Philipp, Parsons, Philip J
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 28.01.2021
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Summary:Due to the importance of the amino ketone motif in synthetic and medicinal chemistry, the number of protocols developed in recent years has considerably increased. This review serves to collate and critically evaluate novel methodologies published since 2011 towards this high value synthon. The chapters are divided by the requisite functionality in the starting material, and an emphasis is placed on discussing functional group compatibility and resultant product substitution patterns. Throughout, applications to medicinal targets are highlighted and mechanistic details are presented, and we further provide a short outlook for future development and emerging potential within this area. This review on α-amino ketone synthesis collates and evaluates developments made in this area over the past decade, with an extended discussion on functional group compatibility, resultant product substitution patterns, and medicinal applications.
Bibliography:Philipp Natho is a PhD student at Imperial College London working under the supervision of Prof. Philip Parsons. He received his M.Sci in Chemistry from Imperial College London where he investigated the total synthesis of morphine under the supervision of Prof. Don Craig. He also worked on the synthesis of highly substituted pyridines under the supervision of Prof. Rick Danheiser at the Massachusetts Institute of Technology. Philipp's current work in the Parsons group is focused on the ring expansion of cyclobutanols to tetralones under transition-metal-free conditions and the application of this technology to natural product synthesis.
Lewis Allen is a postdoctoral research scientist based at Imperial College London. Lewis received his PhD from Imperial College London in 2015 after completing studies on the total synthesis of aphidicolin under the guidance of Prof. Philip Parsons. Lewis was then employed as a senior research scientist at Pareon Chemicals Ltd before becoming an associate principal scientist. Lewis returned to Imperial College London to investigate the synthesis of novel analgesics and cognitive enhancers based on truncated natural products.
Prof. Philip J. Parsons started his independent research career at the University of Southampton in 1979, after completing postdoctoral studies with Prof. Gilbert Stork at Columbia University. While at the University of Southampton, Prof. Parsons cofounded Cookson Chemicals Ltd, now Tocris Bioscience a brand of Bio-Techne. In 1990, he was appointed Professor and Head of Organic Chemistry at the University of Reading. He later moved to the University of Sussex in 1995 where he was appointed Dean of the School of Chemistry, Physics, and Environmental Science. Recently, he was appointed Senior Research Investigator and now Professor at Imperial College London.
Robert-Cristian Raclea is a PhD student at the Massachusetts Institute of Technology. He received his MSci degree from Imperial College London in 2020 after completing his final year research project with Prof. Philip Parsons on the oxidative deconstruction of azetidinols. Robert has also previously conducted synthetic and medicinal chemistry research in the academic groups of Prof. Movassaghi, Prof. Hoelder, Dr Cordier, and Prof. Dinica.
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ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02098b