Article
Chemistry, Multidisciplinary
Martin Berger, Davide Carboni, Paolo Melchiorre
Summary: The study presents the first catalytic enantioselective conjugate addition of allyl groups to alpha, beta-unsaturated aldehydes, utilizing the visible-light-excitation of chiral iminium ions to activate allyl silanes toward the formation of allylic radicals. This radical mechanism overcomes issues seen in traditional conjugate allylation processes and selectively installs prenyl fragments at the beta-carbon of enals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Xiao Lin, Keli Ge, Ningning He, Xuling Chen, Pengfei Li, Mingxin Dong, Wenjun Li
Summary: A chiral phosphoric acid-catalyzed enantioselective aza-addition reaction of arylamines with ketimines has been developed, resulting in the construction of chiral acyclic N,N-acetal motifs. The reaction proceeds smoothly under standard conditions, yielding a series of acyclic N,N-acetals in 82-99% yield with 80-96% ee.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Arun Raj Kizhakkayil Mangadan, Ji Liu, Aaron Aponick
Summary: This study introduces an asymmetric allylic lactonization method using a Pd-II catalyst, which is simple to operate and yields high enantioselectivities up to 99%. This strategy allows for the replacement of a poor leaving group with a potentially better leaving group in the product, avoiding issues with racemization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Adrian Lavios, Amparo Sanz-Marco, Carlos Vila, Gonzalo Blay, Jose R. Pedro
Summary: The spirocyclic motif is widely found in natural products, chiral ligands, and pharmacologically active compounds. The formal [3+2] cycloaddition reaction of isothiocyanates or isocyanides with cyclic compounds has been developed for the enantioselective synthesis of aza-spirocyclic compounds, with organocatalysis playing a key role in these reactions. The synthesis of spirooxindoles using this methodology has received particular attention, highlighting the importance of the structure of the dipolarophiles and the isothiocyanate and isocyanide dipoles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xu Chen, Kaushalendra Patel, Ilan Marek
Summary: An efficient method has been developed for the stereoselective construction of tertiary C-O bonds via stereoinvertive nucleophilic substitution. This method utilizes water, alcohols, and phenols as nucleophiles and demonstrates high tolerance to functional groups, providing a new approach to the formation of highly congested tertiary homoallyl alcohols and ethers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ken-Loon Choo, Bijan Mirabi, Karl Z. Demmans, Mark Lautens
Summary: Enantioenriched spiro-oxiranes with three contiguous stereocenters were synthesized using a rhodium-catalyzed cascade reaction, enabling the formation of a spirocyclic framework in a single step. Both sp(2)- and sp-hybridized carbon nucleophiles were found to be efficient initiators, yielding products with different functional groups. Derivatization studies demonstrated the synthetic versatility of the products' epoxide and alkyne moieties. DFT calculations were employed to explain spectroscopic discrepancies between solution- and solid-state structures of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Mariliis Kimm, Ivar Jarving, Maksim Oseka, Tonis Kanger
Summary: Asymmetric rearrangement reactions are highlighted as a perfect tool for constructing new carbon-carbon bonds in an enantioselective manner. The article specifically discusses a new and straightforward procedure for synthesizing alpha-hydroxy ketones with high diastereo- and enantioselectivity through the enantioselective [2,3]-Wittig rearrangement of cinnamyloxycyclohexanone derivatives catalyzed by a commercially available primary amine.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amol B. Gorde, Anas Ansari, Ramesh Ramapanicker
Summary: New molecules were designed and synthesized to improve the catalytic ability of the catalyst, resulting in high catalytic activity and stereoselectivity under optimized conditions. The studies showed high yields of Michael adducts with excellent enantioselectivities and diastereoselectivities in a wide range of aldehydes and beta-nitrostyrenes.
Article
Chemistry, Physical
Viktoria Kozma, Zsolt Szakonyi, Gyorgy Szollosi
Summary: This study reveals the structural effects of beta-amino acids on the asymmetric Michael additions, including the impact of substituent bulkiness on selectivity, the beneficial arrangement of functional groups in cis isomers, and the influence of nitrogen substituents on reaction rate and enantioselectivity.
Article
Chemistry, Multidisciplinary
Yong-Liang Liu, Xiao-Ping Wang, Ya Li
Summary: A highly selective TMG-catalyzed beta-addition of (arylsulfonyl)fluoromethane derivatives to allenoates has been developed, leading to structurally diverse beta-addition products with a stereogenic fluorinated carbon center.
Article
Chemistry, Multidisciplinary
Vasilis Tseliou, Adriana Faraone, Laura Kqiku, Jan Vilim, Gianluca Simionato, Paolo Melchiorre
Summary: This study introduces a novel strategy for biocascades using a single multifunctional enzyme to promote multiple stereoselective steps in a domino process by mastering distinct catalytic mechanisms, simplifying the synthesis of chiral molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Da Xu, Yu Chang, Yidong Liu, Wenling Qin, Hailong Yan
Summary: This study achieved the enantioselective construction of stable VQM intermediates through organocatalyzed bromination, and revealed the mechanistic details of the two sequential events in VQM-involved reactions. The high potential of VQM as axially chiral synthetic reagents in organic chemistry was demonstrated.
Review
Chemistry, Multidisciplinary
Matthew T. J. Williams, Louis C. Morrill, Duncan L. Browne
Summary: Ball mills input energy by pulverising contents of the jar to samples, while enantioselective organocatalytic reactions proceed through perceived transition states. This review focuses on the combination of organocatalytic reactions with mechanochemical ball milling conditions, with particular emphasis on stereoselectivity control.
Article
Chemistry, Multidisciplinary
En Li, Jiean Chen, Yong Huang
Summary: The Michael reaction is an important method for preparing functional molecules with a β-stereogenic center. However, the enantioselective seleno-Michael addition is still poorly explored. In this study, a highly enantioselective Michael addition reaction of alkyl selenols to enones was reported, introducing a Se atom asymmetrically to an electron-deficient double bond. A chiral bifunctional N-heterocyclic carbene (NHC)/thiourea catalyst was developed and showed remarkable selectivity in delivering chiral β-seleno ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Byungjun Kim, Sukwoo Lee, Sarah Yunmi Lee
Summary: In this study, a new method was reported to successfully promote the catalytic asymmetric Diels-Alder reactions using a chiral catalyst in conjunction with a chiral isothiourea catalyst or a Bronsted acid, resulting in the synthesis of densely functionalized cyclohexenes with multiple stereocenters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Youwei Xie, Gui-Juan Cheng, Sunggi Lee, Philip S. J. Kaib, Walter Thiel, Benjamin List
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
Sunggi Lee, Philip S. J. Kaib, Benjamin List
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Organic
Sunggi Lee, Philip S. J. Kaib, Benjamin List
Article
Multidisciplinary Sciences
Nobuya Tsuji, Jennifer L. Kennemur, Thomas Buyck, Sunggi Lee, Sebastien Prevost, Philip S. J. Kaib, Dmytro Bykov, Christophe Fares, Benjamin List
Article
Chemistry, Multidisciplinary
Sunggi Lee, Han Yong Bae, Benjamin List
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Sunggi Lee, Hyelee Lee, Kian L. Tan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Multidisciplinary
Xixi Sun, Hyelee Lee, Sunggi Lee, Kian L. Tan
Article
Multidisciplinary Sciences
Lucas Schreyer, Philip S. J. Kaib, Vijay N. Wakchaure, Carla Obradors, Roberta Properzi, Sunggi Lee, Benjamin List
Article
Chemistry, Applied
Zdravko Dzambaski, Dimitrios-Ioannis Tzaras, Sunggi Lee, Christoforos G. Kokotos, Bojan P. Bondzic
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Review
Chemistry, Multidisciplinary
Sunggi Lee, Won-jin Chung
Summary: This review provides an overview of the development and application of asymmetric phase-transfer catalysis (PTC) in enantioselective halogenations over the past decade. By utilizing highly ordered ion pairing and hydrogen-bonding interactions, electrophilic and nucleophilic reactions are enabled through a carefully designed chiral phase-transfer catalyst, leading to successful results in fluorination and with heavier halogens.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jaehan Bang, Seyun Gi, Yoonjung Lee, Kian L. Tan, Sunggi Lee
Summary: This study describes the meta-selective C-H functionalization of arylsilanes using a Si-tethered directing group. The method allows for selective alkenylation of arenes with various functional groups, including electron-deficient olefins. Further functional group transformations of the silicon-tethered directing group efficiently produce multi-substituted arenes.
Article
Chemistry, Multidisciplinary
Yujeong Lee, Guilherme L. Tripodi, Donghyun Jeong, Sunggi Lee, Jana Roithova, Jaeheung Cho
Summary: A high-valent manganese(IV)-hydroxo complex was synthesized and characterized in this study. It was found that this complex can activate C-H bonds of aliphatic and aromatic compounds under mild conditions. Detailed kinetic studies revealed that the activation of C-H bonds occurs via rate-determining hydrogen atom abstraction and electron-transfer pathway.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Inorganic & Nuclear
Kyungmin Kim, Seongmin Oh, Donghyun Jeong, Yuri Lee, Dohyun Moon, Sunggi Lee, Jaeheung Cho
Summary: In this study, a series of cobalt(III)-peroxo complexes and cobalt(III)-hydroperoxo complexes were synthesized and characterized. The results showed that their structures and properties were influenced by the electronic effects of the ligands, providing important insights into the electronic nature-reactivity relationship of metal-oxygen species.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Somi Kim, Junhyuk Jo, Sunggi Lee, Won-jin Chung
Summary: In this report, stereochemical modulation was achieved by utilizing pyridine-boryl radical to leave a synthetically modifiable boronate moiety during the cyclization step, leading to a successful catalytic synthesis of trans-2-substituted-1-indanols.
CHEMICAL COMMUNICATIONS
(2023)