Article
Chemistry, Organic
Venkatachalam Pitchumani, Martin Breugst, David W. Lupton
Summary: This study demonstrates the enantioselective conversion of beta-substituted acrylamides to enantioenriched quinolones using electron-withdrawing protection and moderate nucleophilicity N-heterocyclic carbenes. The reaction shows complete diastereoselectivity, good yield, and modest enantioselectivity. Computational studies support the concept of decreased amide bond character with electron-withdrawing protection of the nitrogen.
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
Juan Zhang, Wei Hao, Ying Chen, Zhen Wang, Jinzhong Yao, Weijun Yao
Summary: We have disclosed a method for the construction of exo-bicyclic succinimide derivatives through the Rauhut-Currier reaction and Diels-Alder reaction, exhibiting high stereospecificity and close to quantitative yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Aleksandra Buchcic-Szychowska, Stanislaw Lesniak, Michal Rachwalski
Summary: A series of chiral aziridines with a phosphine moiety were synthesized and used as organocatalysts in the asymmetric intramolecular Rauhut-Currier reactions of p-quinone derivatives. The desired chiral phenols were obtained with high yields and satisfactory enantiomeric excess values.
Article
Chemistry, Organic
Rajkiran Kumari, Ajit Kumar Jha, Sophiya Goyal, Reena Maan, S. Rajagopala Reddy, Srinivasan Easwar
Summary: A serendipitous Rauhut-Currier dimerization of 1,1-disubstituted activated olefins was observed in the presence of DABCO. The reaction produces multifunctionalized enol esters with yields greater than 90% in most cases, without the need for column chromatographic purification. The acyl transfer is believed to occur via a Morita-Baylis-Hillman (MBH) reaction transition state, supported by computational calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sei-Hyun Choi, Byungsun Jeon, Namho Kim, Hsin-Hui Wu, Tzu-Ping Ko, Mark W. Ruszczycky, Eta A. Isiorho, Yung-Nan Liu, Adrian T. Keatinge-Clay, Ming-Daw Tsai, Hung-Wen Liu
Summary: The catalog of enzymes catalyzing nucleophile-assisted formation of C-C bonds is limited, with no definitive example of a biological RauhutCurrier reaction known. SpnL, in conjunction with SpnF, is implicated in catalyzing a potential biological Rauhut-Currier reaction, but further research is needed to fully understand the mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Satish B. Thopate, Lakshmi Revati Magham, Shrabani Dinda, Rambabu Chegondi
Summary: This work presents the development of an unconventional and highly enantioselective solvent-promoted Rauhut-Currier cyclization of enal-tethered cyclohexadienone. The reaction involves the reactivity of a Jorgensen-Hayashi catalyst through the merging of iminium and enamine activation. The asymmetric desymmetrization reaction shows broad substrate scope with good yields and high to excellent enantioselectivity. DFT calculations suggest that the rate-limiting step is the elimination of the alkoxy group, which proceeds through proton abstraction by solvent instead of a direct 1,3-proton shift.
Article
Chemistry, Organic
Juan Ye, Yang Wang
Summary: A comprehensive study on the mechanisms and origins of the chemoselectivity and regioselectivity of phosphine-catalyzed Rauhut-Currier reaction is performed by DFT. The computational results reveal that the cross R-C reaction is energetically favorable, with head-to-tail product being generated preferentially. The C-C bond formation process is identified as the determining step for regioselectivity and chemoselectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Gyumin Kang, Sangbin Park, Sunkyu Han
Summary: Securinega alkaloids have attracted the attention of the synthetic community due to their structural diversity and notable bioactivities. The synthesis of high-order Securinega alkaloids and oxidized derivatives has been relatively unexplored, but this Account describes the development of reliable synthetic methods, including accelerated Rauhut-Currier reactions and cross-coupling/conjugate reduction-based dimerization strategies. Additionally, the achievement in the synthesis of high-oxidation state Securinega alkaloids is depicted, including oxidative transformations and fragment-coupling strategies. These methods and strategies have broad applicability to other alkaloids and can expand the chemical space of secondary metabolites.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Dragana Stevanovic, Jovana Bugarinovic, Marko Pesic, Anka Todosijevic, Goran A. Bogdanovic, Ivan Damljanovic
Summary: A simple protocol has been developed for the synthesis of multifunctional ferrocene derivatives. The study showed that the strong electron-donating group at the beta-position of nitroalkenes prevents polymerization and stabilizes the intermediate.
Article
Chemistry, Organic
Nimisha Bania, Buddhadeb Mondal, Sounak Ghosh, Subhas Chandra Pan
Summary: In this study, unsaturated pyrazolones were used in the Rauhut-Currier reaction for the first time, leading to the successful synthesis of trisubstituted tetrahydropyrano[2,3-c]pyrazoles with excellent diastereoselectivities. The synthesis of disubstituted tetrahydropyrano[2,3-c]pyrazoles was also demonstrated, and a catalytic asymmetric version of the process was preliminarily studied using chiral DMAP catalysts.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Snehal Pednekar, Sudheesh T. Sivanandan, Deepak Kumar, Raveendran Bharath Krishna, Irishi N. N. Namboothiri
Summary: A facile, base-and catalyst-free synthesis of Morita-Baylis-Hillman and Rauhut-Currier adducts of fi-aminonitroalkenes with different electrophiles is reported. The reactions with ethyl glyoxylate, trifluoropyruvate, ninhydrin, vinyl sulfone, and N-tosylazadiene result in good to excellent yields of products at room temperature. The adducts of ninhydrin and fi-aminonitroalkene spontaneously cyclize to fused indenopyrroles. Gram-scale reactions and synthetic transformations of the adducts are also reported.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhibing Weng, Ying Zhou, Xin Yue, Feng Jiang, Wengang Guo
Summary: In this study, catalytic asymmetric alpha-regioselective Michael additions of vinylogous alpha-ketoester enolates were conducted efficiently using a chiral bifunctional organocatalyst. The reactions yielded Rauhut-Currier type products with high yields and excellent regio- and enantioselectivities.
Article
Chemistry, Multidisciplinary
Wu-Wei Dong, Kui Tian, Xiu-Qin Dong, Chun-Jiang Wang
Summary: A series of structurally novel multifunctional chiral aminophosphine catalysts were developed through a concise synthetic strategy. These catalysts were successful in catalyzing the highly enantioselective intermolecular cross Rauhut-Currier reactions between vinyl ketones and 3-acyl acrylates and 2-ene-1,4-diones, generating a wide range of structurally important chiral multicarbonyl products with high stereocontrol.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Yue Lu, Ningtao He, Xiaohe Miao, De Wang
Summary: The novel chiral phosphine-catalyzed cross Rauhut-Currier reactions provide a versatile approach for the synthesis of multifunctional compounds. The reaction exhibits broad substrate scope and moderate-to-excellent enantioselectivity control. It also shows promising applications in the synthesis of drug and useful compounds due to its tolerance towards natural product and drug derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Kathryn L. Olsen, Matthew R. Jensen, James A. MacKay
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Multidisciplinary
James A. MacKay, Nicholas R. Wetzel
JOURNAL OF CHEMICAL EDUCATION
(2014)
Article
Chemistry, Organic
Trisha A. Duffey, James A. MacKay, Edwin Vedejs
JOURNAL OF ORGANIC CHEMISTRY
(2010)
Article
Chemistry, Organic
Vikram Bhat, James A. MacKay, Viresh H. Rawal
Article
Chemistry, Organic
Vikram Bhat, James A. MacKay, Viresh H. Rawal
Article
Chemistry, Multidisciplinary
Venubabu Kotikam, Scott D. Kennedy, James A. MacKay, Eriks Rozners
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Ilze Kumpina, Nikita Brodyagin, James A. MacKay, Scott D. Kennedy, Martins Katkevics, Eriks Rozners
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Nikita Brodyagin, Aubrey L. Maryniak, Ilze Kumpina, John M. Talbott, Martins Katkevics, Eriks Rozners, James A. MacKay
Summary: Peptide nucleic acids (PNA) with extended isoorotamides containing nucleobases (I-o) were designed to bind A-U base pairs in double-stranded RNA. Isothermal titration calorimetry and UV thermal melting experiments showed improved affinity for A-U using the Io scaffold in PNA, with PNAs having four sequential Io extended nucleobases maintaining high binding affinity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
John M. Talbott, Brandon R. Tessier, Emily E. Harding, Grant D. Walby, Kyle J. Hess, Vladislavs Baskevics, Martins Katkevics, Eriks Rozners, James A. Mackay
Summary: Four new isoorotamide (Io)-containing PNA nucleobases have been designed for A-U recognition of double helical RNA. The experiments showed that these new PNA nucleobases have strong binding affinity, which will contribute to the future design of nucleobases capable of recognizing any sequence of double helical RNA.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
JA MacKay, E Vedejs
JOURNAL OF ORGANIC CHEMISTRY
(2006)
Article
Chemistry, Organic
JA MacKay, RL Bishop, VH Rawal
Article
Chemistry, Organic
JA MacKay, E Vedejs
JOURNAL OF ORGANIC CHEMISTRY
(2004)
Article
Chemistry, Organic
E Vedejs, O Daugulis, LA Harper, JA MacKay, DR Powell
JOURNAL OF ORGANIC CHEMISTRY
(2003)
Article
Chemistry, Organic
E Vedejs, O Daugulis, JA Mackay, E Rozners
