Review
Chemistry, Organic
Helene Pellissier
Summary: Organocatalytic dynamic kinetic resolution (DKR) has emerged as a promising field in the past two decades, allowing efficient separation of chiral compounds. This review aims to provide an update on organocatalytic DKRs since 2016.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biotechnology & Applied Microbiology
Chenming Huang, Junling Liu, Jiali Fang, Xian Jia, Zhendong Zheng, Song You, Bin Qin
Summary: This review discusses the advances in the research area of KRED-catalyzed asymmetric synthesis for biomanufacturing of chiral chemicals with at least two chiral centers through the kinetic resolution (KR) approach and the dynamic kinetic resolution (DKR) approach.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Shutao Sun, Yingang Ma, Ziqiang Liu, Lei Liu
Summary: A novel manganese-catalyzed oxidative kinetic resolution method was reported, which effectively reacts asymmetric C(sp(3))-H oxidation to distinguish different types of cyclic benzylic ethers with wide application prospects and high enantiodiscrimination efficiency. This study further explores the direct late-stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Pedro P. De Castro, Gabriel M. F. Batista, Giovanni W. Amarante, Helio F. Dos Santos
Summary: Theoretical calculations and control experiments were used to investigate the mechanism and origin of enantioselectivity in the phosphoric-acid-catalyzed dynamic kinetic resolution of azlactones. The results identified a Munchnone intermediate as crucial in the isomerization of azlactone rings, and the developed model successfully predicted enantioselectivity under various reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yanshun Li, Nanxing Gao, Guorui Cao, Dawei Teng
Summary: The Mukaiyama-Mannich reaction of enol silyl ether with cyclic N-sulfonyl ketimino ester was catalyzed by a cobalt complex of a chiral spiroBox ligand. Excellent yields (up to 99%) and ee values (up to 99%) were achieved with a wide range of substrates. This catalytic system allows for the facile synthesis of quaternary alpha-amino acid derivatives with high yields and excellent enantioselectivities.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Patricia Rodriguez-Salamanca, Gonzalo de Gonzalo, Jose A. Carmona, Joaquin Lopez-Serrano, Javier Iglesias-Siguenza, Rosario Fernandez, Jose M. Lassaletta, Valentin Hornillos
Summary: This article describes a highly enantioselective biocatalytic dynamic kinetic resolution (DKR) for configurationally labile N-arylindole aldehydes. The DKR is achieved through atroposelective bioreduction of the carbonyl group using commercial ketoreductases (KREDs), resulting in axially chiral N-arylindole aminoalcohols with excellent conversions and optical purities. The strategy relies on the racemization of the stereogenic axis facilitated by a transient Lewis pair interaction between NMe2 and the aldehyde groups. This protocol offers a broad substrate scope under mild conditions.
Article
Chemistry, Applied
Izabela Weglarz, Karol Michalak, Jacek Mlynarski
Summary: The study reported the first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex, achieving pharmaceutically relevant enantioenriched 2-aryl-substituted pyrrolidines with excellent enantioselectivities. The synthetic utility of the presented methodology was demonstrated in an efficient synthesis of pharmaceutical drug precursors to Aticaprant and Larotrectinib.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jose A. Carmona, Patricia Rodriguez-Salamanca, Rosario Fernandez, Jose M. Lassaletta, Valentin Hornillos
Summary: An atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes is achieved by transfer hydrogenative coupling of allyl acetate. The reaction leads to the installation of central and axial chirality, with high diastereoselectivities and excellent enantioselectivities when ortho-cyclometalated iridium-DM-BINAP is used as the catalyst. The racemization of the substrates is facilitated through a designed transient Lewis acid-base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jan Seliger, Martin Oestreich
Summary: A novel approach for the dynamic kinetic resolution of benzylic alcohols was reported, achieving enantioselective silylation of racemic alcohol mixtures in high yields by merging different catalytic processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jihoon Moon, Takusho Kin, Karin Mizuno, Shuji Akai, Kyohei Kanomata
Summary: This study presents a chemoenzymatic dynamic kinetic resolution (DKR) of racemic sec-alcohols using immobilized lipase and aqueous sulfuric acid as catalysts for kinetic resolution and racemization, respectively. The use of nanoparticle-stabilized phase separation in a Pickering emulsion allowed the use of these incompatible catalysts in a single vessel. The racemization reaction in the aqueous sulfuric acid solution effectively suppressed side reactions, resulting in high yields and optical purities.
Article
Chemistry, Multidisciplinary
Fuzhuo Li, Li-Cheng Yang, Jingyang Zhang, Jason S. Chen, Hans Renata
Summary: A highly diastereo- and enantioselective biocatalytic transamination method was developed for the preparation of a broad range of aromatic beta-branched alpha-amino acids. The transformation proceeds through dynamic kinetic resolution unique to the optimal enzyme, showcasing its utility for the synthesis of sp(3)-rich cyclic fragments and total synthesis of jomthonic acid A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Linlong Dai, Yuheng Liu, Qing Xu, Meifang Wang, Qiaohong Zhu, Peiyuan Yu, Guofu Zhong, Xiaofei Zeng
Summary: This paper presents a dynamic kinetic resolution method for the synthesis of axially chiral diaryl ethers. By using a Bronsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction, the desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79%) and high enantioselectivities (up to 95% ee) under standard reaction conditions. These structural motifs are interesting precursors for further transformations and may have potential applications in the synthesis of chiral ligands or catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Benjamin Poelloth, Mukund P. Sibi, Hendrik Zipse
Summary: The factors responsible for the kinetic resolution of alcohols by chiral pyridine derivatives have been elucidated through accurate competitive linear regression analysis. Increasing the size of the aromatic side chain accelerates the reaction rate of the major enantiomer, leading to the design of a new catalyst with increased steric bulk for higher enantioselectivity values. Experimental and theoretical results suggest that the enhancement of enantioselectivity is achieved by accelerating the transformation of the major enantiomer through attractive non-covalent interactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ting Liu, Xiangqing Feng, Haifeng Du
Summary: A metal-free hydrosilylation reaction has been developed to synthesize optically active amines in high yields with up to 73% enantiomeric excess. Moreover, a chiral borane-catalyzed asymmetric hydrosilylation of vicinal diimines has also been achieved, providing cis-1,2-diamines with 12-70% enantiomeric excess.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Physical
Jose A. Carmona, Carlos Rodriguez-Franco, Joaquin Lopez-Serrano, Abel Ros, Javier Iglesias-Siguenza, Rosario Fernandez, Jose M. Lassaletta, Valentin Hornillos
Summary: An efficient dynamic kinetic resolution (DKR) approach has been developed for the synthesis of axially chiral diamines based on ruthenium-catalyzed enantioselective transfer hydrogenation. This method features a broad substrate scope and proceeds under very mild conditions, allowing the preparation of BINAM homologues in good to high yields and nearly perfect enantioselectivities (up to 99% ee).
Article
Chemistry, Organic
Ibrahim U. Kutama, Simon Jones
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
R. A. Bawa, F. -M. Gautier, H. Adams, A. J. H. M. Meijer, S. Jones
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Cell Biology
Anne L. Robertson, Nikolay V. Ogryzko, Katherine M. Henry, Catherine A. Loynes, Matthew J. Foulkes, Marco M. Meloni, Xingang Wang, Christopher Ford, Malcolm Jackson, Philip W. Ingham, Heather L. Wilson, Stuart N. Farrow, Roberto Solari, Roderick J. Flower, Simon Jones, Moira K. B. Whyte, Stephen A. Renshaw
DISEASE MODELS & MECHANISMS
(2016)
Article
Chemistry, Organic
Rebecca C. Collins, Martyn N. Paley, Gillian M. Tozer, Simon Jones
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Inorganic & Nuclear
Christopher J. A. Warner, Andrew T. Reeder, Simon Jones
TETRAHEDRON-ASYMMETRY
(2016)
Article
Radiology, Nuclear Medicine & Medical Imaging
Steven Reynolds, Stephen Metcalf, Edward J. Cochrane, Rebecca C. Collins, Simon Jones, Martyn N. J. Paley, Gillian M. Tozer
MAGNETIC RESONANCE IN MEDICINE
(2017)
Article
Chemistry, Organic
X. Li, A. T. Reeder, F. Torri, H. Adams, S. Jones
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Biology
Victoria A. Lund, Katarzyna Wacnik, Robert D. Turner, Bryony E. Cotterell, Christa G. Walther, Samuel J. Fenn, Fabian Grein, Adam J. M. Wollman, Mark C. Leake, Nicolas Olivier, Ashley Cadby, Stephane Mesnage, Simon Jones, Simon J. Foster
Article
Multidisciplinary Sciences
Matthew J. Foulkes, Katherine M. Henry, Julien Rougeot, Edward Hooper-Greenhill, Catherine A. Loynes, Phil Jeffrey, Angeleen Fleming, Caroline O. Savage, Annemarie H. Meijer, Simon Jones, Stephen A. Renshaw
SCIENTIFIC REPORTS
(2017)
Article
Chemistry, Organic
Alexander M. Fields, Simon Jones
Article
Chemistry, Organic
Christopher J. A. Warner, Sian S. Berry, Simon Jones
Article
Multidisciplinary Sciences
Matthew J. Foulkes, Faith H. Tolliday, Katherine M. Henry, Stephen A. Renshaw, Simon Jones
Article
Multidisciplinary Sciences
Peter Oatley, Joseph A. Kirk, Shuwen Ma, Simon Jones, Robert P. Fagan
SCIENTIFIC REPORTS
(2020)
Review
Chemistry, Organic
Sian S. Berry, Simon Jones
Summary: Chiral substituted pyrrolidines are key elements in biologically active molecules and are often synthesized using kinetic resolution methods to obtain enantiomerically pure compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Ray Jenkinson, Ashley James Cadby, Simon Jones
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
