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)
Review
Chemistry, Multidisciplinary
Subhankar Biswas, Nimisha Bania, Subhas Chandra Pan
Summary: Intermolecular cross Rauhut-Currier reactions have gained significant attention in recent years due to their ability to produce complex structures with good regio- and stereo- selectivity using various catalysts. This review highlights the recent developments in these reactions, involving both achiral and chiral catalysts, resulting in products with diverse utilities. Furthermore, detailed mechanistic studies of these reactions are also presented.
Article
Chemistry, Multidisciplinary
Chiara Portolani, Giovanni Centonze, Sara Luciani, Andrea Pellegrini, Paolo Righi, Andrea Mazzanti, Alessia Ciogli, Andrea Sorato, Giorgio Bencivenni
Summary: The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol, providing a stereodivergent approach to enantioenriched atropisomeric hydrazides. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol, demonstrating the effectiveness of this strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Samuel M. Smith, Mark D. Greenhalgh, Taisiia Feoktistova, Daniel M. Walden, James E. Taylor, David B. Cordes, Alexandra M. Z. Slawin, Paul Ha-Yeon Cheong, Andrew D. Smith
Summary: This study reports the full scope and limitations of catalytic acylative kinetic resolution of a range of tertiary heterocyclic alcohols using a commercially available Lewis basic isothiourea catalyst. The protocol is highly effective for the synthesis of enantioenriched compounds and a detailed kinetic analysis of the reaction mechanism has been provided.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Takeshi Suzuki, Manaya Iwakura, Kenya Nakata
Summary: The chiral guanidine catalyzed silylative kinetic resolution of racemic trans-2-alkyl-1-indanols using Ph3SiCl achieved high selectivity and activity. The relative stereochemistry of the stereogenic centers of the substrates was important for the reaction, with only trans-substrates selectively undergoing the reaction.
Article
Chemistry, Organic
Miglena K. Georgieva, A. Gil Santos
Summary: The Diels-Alder reaction is a fascinating chemical process that has been extensively studied, both in its achiral and chiral versions. In this study, the authors investigate the Diels-Alder reaction of 2'-hydroxychalcones with two dienes, catalyzed by chiral organo-boron Lewis acid complexes. The authors use theoretical methods to evaluate the proposed reaction mechanism and provide insights into the enantioselectivity and endo/exo selectivity of the reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dan Hu, Si Bei Poh, Feipeng Liu, Zhifeng Tu, Xia Wang, Shenci Lu, Yu Zhao
Summary: The effect of counter-anions on enantio-control in oxidative NHC catalysis is systematically investigated in this study. The results demonstrate that the identity of counter-anions has a significant impact on the enantioselectivity of the catalytic system, and highly efficient kinetic resolution can be achieved by selecting appropriate counter-anions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Titouan Desrues, Xueyang Liu, Jean-Marc Pons, Valerie Monnier, Jean-Arthur Amalian, Laurence Charles, Adrien Quintard, Cyril Bressy
Summary: This study introduces a new method for the enantioselective synthesis of tertiary alcohols through a chiral isothiourea catalyzed selective acylation of adjacent secondary alcohols, allowing for the preparation of highly enantioenriched monoesters and starting diols. The approach enables the kinetic resolution of racemic diastereoenriched secondary/tertiary diols with s-values exceeding 200.
Article
Chemistry, Physical
Jae Ho Shim, Seok Hyun Cheun, Hyeon Soo Kim, Deok-Chan Ha
Summary: Michael addition is a significant reaction for synthesizing natural products or complex compounds with biological activities. In this study, a selective Michael addition reaction was achieved by using thiourea as an organic catalyst and double activation mechanism. The reaction exhibited high degree of enantioselectivity and diastereoselectivity, leading to the formation of Michael products with excellent yields.
Article
Chemistry, Organic
Ling-Fei Tao, Linghui Qian, Jia-Yu Liao
Summary: In this study, an unprecedented silver-catalyzed highly diastereo- and enantioselective [3+3] cycloaddition of activated isocyanides with azomethine imines was developed. This method features high efficiency, good to excellent stereocontrol, wide substrate scope, as well as operational simplicity. It is also noteworthy that the same catalytic system was proved to be suitable for not only the late-stage functionalization of complex bioactive molecules but also the kinetic resolution of racemic azomethine imines.
Review
Chemistry, Organic
Gangavara L. Thejashree, Eric Doris, Edmond Gravel, Irishi N. N. Namboothiri
Summary: Kinetic resolution and dynamic kinetic resolution are common methods to access enantiomerically enriched compounds, with the latter achieving complete transformation through the process of racemization and further resolution. This review summarizes the dual catalytic strategies applied in kinetic resolution and dynamic kinetic resolution, focusing on the role of the two catalysts, compatibility between them, and practical benefits.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yunnan Xu, Yicong Luo, Jianxun Ye, Yu Deng, Delong Liu, Wanbin Zhang
Summary: Sequential asymmetric hydrogenation of 3-amino-4-chromones using Rh catalyst has been achieved for the first time. The process involves an unprecedented dynamic kinetic resolution under neutral conditions, resulting in high yields of (S,R)-3-amino-4-chromanols with excellent enantio- and diastereoselectivities. Mechanistic studies suggest that the process proceeds via stereomutation pathway rather than traditional racemization.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Hyung-Joon Kang, Changseok Lee, Sungwoo Hong
Summary: Kinetic resolution is a powerful strategy for isolating enantioenriched compounds from mixtures, and the development of selective catalytic processes is an active research area. In this study, a nickel-catalyzed kinetic resolution of racemic alpha-substituted unconjugated carbonyl alkenes was achieved through enantio-, diastereo-, and regioselective hydroamination, resulting in chiral alpha-substituted butenamides and syn-beta(2,3)-amino acid derivatives with high enantiomeric purity (up to 99% ee) and selectivity factor up to >684. The unique structure of the chiral nickel complex plays a key role in the efficient kinetic resolution and enantioselective bond construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Soumik De, Abhinav Jain, Pranjit Barman
Summary: The Schiff base and its metal complexes are versatile compounds with adaptable metal chelating properties. The chiral Schiff base complexes exhibit excellent stability in high temperatures and can induce stereochemistry in different chemical reactions for synthesizing highly optically active compounds.
Article
Chemistry, Multidisciplinary
Arka Porey, Bhaskar Deb Mondal, Joyram Guin
Summary: Enantioenriched acyclic alpha-substituted beta-hydroxy amides were successfully synthesized via enantioselective acylation of primary alcohol with N-heterocyclic carbene, with enhanced selectivity achieved by using cyclic tertiary amine as base additive. Diastereomeric transition state models were proposed to rationalize the origin of enantioselectivity in the catalytic kinetic resolution process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Raju Jannapu Reddy, Md. Waheed, Thatikonda Karthik, Angothu Shankar
NEW JOURNAL OF CHEMISTRY
(2018)
Article
Chemistry, Organic
Raju Jannapu Reddy, Angothu Shankar, Md Waheed, Jagadeesh Babu Nanubolu
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Organic
Raju Jannapu Reddy, Angothu Shankar, Arram Haritha Kumari
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Applied
Raju Jannapu Reddy, Jangam Jagadesh Kumar, Arram Haritha Kumari, Gamidi Rama Krishna
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Applied
Raju Jannapu Reddy, Md Waheed, Arram Haritha Kumari, Gamidi Rama Krishna
Summary: A copper(I)-catalyzed interrupted click-sulfenylation reaction has been developed for the synthesis of triazole-fused eight-membered heterocycles from O-/N-propargyl benzyl thiosulfonates and organic azides. The method provides good to high yields of the products under mild reaction conditions and can also achieve a three-component reaction for fused-triazole synthesis. The protocol has been demonstrated at gram-scale reactions and a plausible mechanism has been proposed based on experimental results.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Raju Jannapu Reddy, Angothu Shankar, Jangam Jagadesh Kumar, Nunavath Sharadha, Gamidi Rama Krishna
Summary: A practical and efficient oxidative dual C-H sulfenylation method using odorless and inexpensive elemental sulfur in DMSO has been reported for the synthesis of sulfur-bridged imidazoheterocycles under metal-free conditions. The reaction exhibited a broad substrate scope with good functional group tolerance, and gram-scale reactions have been successfully carried out.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Raju Jannapu Reddy, Arram Haritha Kumari, Nunavath Sharadha, Gamidi Rama Krishna
Summary: This study explores the asymmetric sulfuration reaction of (E)-beta-iodovinyl sulfones with thiols in different solvent environments, and develops a fast assembly method for saturated/unsaturated dithioalkenes and thiosulfonylalkenes. The method is simple, high-yielding, and has a wide substrate adaptability and functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Raju Jannapu Reddy, Arram Haritha Kumari, Gamidi Rama Krishna
Summary: A new class of 1,6-enyne-containing propargylic alcohols has been designed and synthesized for the direct synthesis of 3-alkenyl benzoheteroles. The reactions involving Ag-catalyzed cascade radical sulfonylative-cycloannulation and three-component coupling have provided efficient access to a wide range of benzoheterole derivatives. The scalability of the reaction and its compatibility with late-stage synthetic transformations have been successfully demonstrated. A plausible mechanism is proposed based on experimental results and control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Raju Jannapu Reddy, Jangam Jagadesh Kumar, Arram Haritha Kumari
Summary: A base-mediated one-pot reaction involving oxaMichael addition-elimination, cycloisomerization, and stereoselective sulfonyl migration has been developed for the synthesis of vinyl sulfonetethered chromenes. The reaction exhibited good functional group compatibility and gram-scale robustness, and the corresponding postsynthetic transformations were successful. Plausible mechanistic pathways were proposed based on experimental results.
Article
Chemistry, Organic
Raju Jannapu Reddy, Nunavath Sharadha, Arram Haritha Kumari
Summary: Pyrazolo[1,5-a]pyridines continue to play an important role in medicinal chemistry, but the direct synthesis of 3-sulfonyl analogues has not been explored. In this study, a method for the synthesis of 2-substituted pyrazolo[1,5-a]pyridines was developed using (E)-beta-iodovinyl sulfones and 1-aminopyridinium iodide. Additionally, a modification of the dipolar N-tosylpyridinium imide allowed for the preparation of 3-sulfonyl-pyrazolo[1,5-a]pyridines. The metal-free protocol demonstrated a wide substrate scope and good functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Angothu Shankar, Md. Waheed, Raju Jannapu Reddy
Summary: A highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita-Baylis-Hillman (MBH) adducts and thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series of ally! sulfones in good to high yields with high stereoselectivities. A wide variety of MBH bromides/acetates as well as thiosulfonates were tolerated and reliable in scaled-up synthesis.
Review
Chemistry, Multidisciplinary
Raju Jannapu Reddy, Arram Haritha Kumari
Summary: Sodium sulfinates have been developed as versatile building blocks for the synthesis of various organosulfur compounds, showing significant progress in the preparation of sulfonates, sulfonamides, and sulfones.
Review
Chemistry, Organic
Raju Jannapu Reddy, Arram Haritha Kumari, Jangam Jagadesh Kumar
Summary: This review focuses on recent advancements in the preparation and synthetic applications of beta-keto sulfones, with an emphasis on direct construction methods and versatile characteristics, as well as the synthesis prospects and multifunctionality of beta-keto thiosulfones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Raju Jannapu Reddy, Md Waheed, Gamidi Rama Krishna
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Raju Jannapu Reddy, Md. Waheed, Jangam Jagadesh Kumar
