Article
Chemistry, Organic
Jigyansa Sahoo, Jeetendra Panda, Santanab Giri, Gokarneswar Sahoo
Summary: An investigation into the sensitivity of reaction conditions to a highly utilized protocol has been reported. The mono-Boc functionalization of prolinol can be controlled for the exclusive synthesis of N-Boc, O-Boc, or oxazolidinone derivatives. A successful chemoselective functionalization of the nucleophilic sites of prolinol by exploiting the relative acidity difference of NH and OH along with the reversed nucleophilicity of the corresponding conjugate bases N- and O- is reported. This protocol has also been used for the synthesis of several O-functionalized prolinol derived organocatalysts, few of which have been newly reported.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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
Ramarao Parella, Satish Jakkampudi, Pranjal Bora, Nagaraju Sakkani, John C. -G. Zhao
Summary: (English Summary:)
The study revealed that modularly designed organocatalysts (MDOs) can facilitate the domino Michael/Michael reaction with switchable enamine and iminium catalytic modes. By utilizing appropriate combinations of precatalyst modules and reaction conditions, both catalytic modes can be individually switched on and off. Under optimized conditions with both enamine and iminium catalysis modes activated, the desired domino reaction products can be obtained with good yields and stereoselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kiran Kumari, Meeta Bhati, Roopendra Singh Madhukar, Akram Gulam Hussain Khan, Prachi Janjani, S. Rajagopala Reddy, Srinivasan Easwar
Summary: A sulfonamide moiety was introduced at the C-4 position of proline, cis to the -COOH group, to investigate a possible synergistic interaction between the two functional groups and its consequent influence on the enamine mediated asymmetric aldol reaction. The results demonstrate that the resulting catalyst is capable of efficiently producing aldol adducts with excellent diastereo- and enantioselectivities in the presence of water.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kiran Kumari, Meeta Bhati, Roopendra Singh Madhukar, Akram Gulam Hussain Khan, Prachi Janjani, S. Rajagopala Reddy, Srinivasan Easwar
Summary: A sulfonamide moiety was introduced at the C-4 position of proline, cis to the -COOH group, to investigate the potential synergistic interaction between the two functional groups and its influence on the enamine mediated asymmetric aldol reaction. The resulting catalyst exhibited high efficiency in producing aldol adducts with excellent diastereo- and enantioselectivities in the presence of water. Computational study was also conducted to gain further insights into the proposed cooperative assistance.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Dmitri Trubitson, Jevgenija Martonova, Marina Kudrjasova, Kristin Erkman, Ivar Jarving, Tonis Kanger
Summary: An efficient enantioselective organocatalytic method has been developed for the synthesis of N-alkylated indoles with alpha-branched alkyl substituents from unsaturated indolyl ketones via a Michael addition. The resulting products exhibit high enantioselectivities and good yields, with tolerance towards various nucleophiles and substitution patterns of the indole ring. Both electron-withdrawing and electron-donating substituents can be accommodated at any position of the heteroaromatic ring.
Article
Chemistry, Organic
Huifang Song, Yuli Sun, Chengrong Lu, Bei Zhao
Summary: Chiral dinuclear rare-earth metal complexes were synthesized and three unknown complexes were characterized. These chiral complexes showed high reactivity in the asymmetric hydrophosphonylation reaction, with complex 7 and chiral diamine proving to be the optimal catalyst combination. The reaction yielded hydrophosphonylation products with high yields and excellent enantiomeric excess values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Jasmine Sinha, Shafer Soars, Christopher N. Bowman
Summary: This article describes an efficient enamine organocatalyzed thiol-Michael click reaction and its broad application in cross-linking polymerizations. The nucleophilicity of the enamines used is crucial for the reaction efficiency and overall yields, with in situ formation of an enamine via photo-deprotection of an amine showing promising results in facilitating thiol-Michael reactions and improving functional group conversion rates.
Article
Chemistry, Multidisciplinary
Zubeda Begum, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: Distinct boron fused primary amino amide organocatalysts were synthesized from commercially available amino acids. These catalysts showed good catalytic activities in asymmetric crossed aldol reaction, producing corresponding chiral anti-aldol adducts with high chemical yields, moderate diastereoselectivity, and good to excellent enantioselectivities (up to 94% yields, up to 90:10 dr, up to 94% ee).
Article
Chemistry, Organic
Eun Chae Son, Seung Yeon Kim, Sung-Gon Kim
Summary: Organocatalytic enantioselective intramolecular oxa-Michael reactions can efficiently produce 1,3-dihydroisobenzofuranyl-1-methylene ketones and esters with high yields and enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sheng Zhang, Wenchao Gao, Jianxue Shi, Jingjing Li, Fengyi Li, Yating Liang, Xuan Zhan, Man-Bo Li
Summary: An umpolung addition of dicyanobenzene to alpha,beta-unsaturated alkenes has been developed using an electroreductive strategy. The electrochemical protocol is compatible with challenging substrates, and good regioselectivities are observed in the reaction. The synthetic utility of this electrochemical approach is demonstrated by direct functionalization of two compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Yuping Wang, Jinsong Han, Yu Liu, Panpan Zhang, Wanyao Wei, Yajun Jian
Summary: A novel systematic on water Michael addition reaction using alpha,beta-unsaturated ketone and nitromethane was developed by introducing an N-methyl imidazole group to enhance electrophilic activity, leading to a higher reaction rate in water. The results suggest that N-methyl imidazole bearing substrates are prone to form hydrogen bonds with water, providing insights for selecting suitable substrates for on water reactions.
Article
Chemistry, Multidisciplinary
Jose A. C. Delgado, Fidel E. M. Vicente, Alexander F. de la Torre, Vitor A. Fernandes, Arlene G. Correa, Marcio W. Paixao
Summary: In this study, a library of N-alkylated lipopeptide organocatalysts were synthesized through an isocyanide-based multicomponent reaction. These catalysts were evaluated in the 1,4-addition of aldehydes to trans-beta-nitrostyrene using water as the sole solvent, resulting in excellent yields, diastereoselectivities, and enantioselectivities under sustainable reaction conditions with low catalyst loadings and without additives.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Yoseop Kim, Seung Yeon Kim, Sung-Gon Kim
Summary: A new asymmetric annulation reaction was developed to efficiently synthesize enantioenriched polyheterotricyclic imidazolidines and oxazolidines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zubeda Begum, Haruka Sannabe, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: Simple primary beta-amino alcohols act as efficient organocatalysts in the asymmetric Michael addition of beta-keto esters with nitroalkenes, producing highly pure chiral Michael adducts. The choice of catalyst and reaction temperature determines the enantiomeric outcome of the adducts.
Article
Chemistry, Multidisciplinary
Lu Ping, Feng Chao, Loh Teck-Peng
ACTA CHIMICA SINICA
(2015)
Article
Chemistry, Multidisciplinary
Li-Ying Zhang, Jia-Hui Zhou, Yun-He Xu, Teck-Peng Loh
CHEMISTRY-AN ASIAN JOURNAL
(2015)
Correction
Chemistry, Multidisciplinary
Min Wang, Xiang Zhang, Yu-Xuan Zhuang, Yun-He Xu, Teck-Peng Loh
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Min Wang, Zheng-Li Liu, Xiang Zhang, Pan-Pan Tian, Yun-He Xu, Teck-Peng Loh
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Min Wang, Xiang Zhang, Yu-Xuan Zhuang, Yun-He Xu, Teck-Peng Loh
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Xu-Hong Hu, Jian Zhang, Xiao-Fei Yang, Yun-He Xu, Teck-Peng Loh
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Organic
Shichao Ren, Chao Feng, Teck-Peng Loh
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Chemistry, Organic
Ming-Zhu Lu, Cheng-Qiang Wang, Teck-Peng Loh
Article
Chemistry, Organic
Xiang Zhang, Min Wang, Ran Ding, Yun-He Xu, Teck-Peng Loh
Article
Chemistry, Organic
Sheng-Qi Qiu, Yun-He Xu, Teck-Peng Loh
Article
Chemistry, Organic
Xiao-Fei Yang, Xu-Hong Hu, Teck-Peng Loh
Article
Chemistry, Organic
Pan-Pan Tian, Sai-Hu Cai, Qiu-Ju Liang, Xing-Yi Zhou, Yun-He Xu, Teck-Peng Loh
Article
Chemistry, Organic
Ming-Xin Zhang, Xu-Hong Hu, Yun-He Xu, Teck-Peng Loh
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Jun-Kee Cheng, Teck-Peng Loh
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Zhenguo Zhang, Jun Gu, Yongheng Lv, Liang Ji, Xiaoxiao Liu, Beishen Wu, Fang Liu, Zhenhua Jia, Teck-Peng Loh
Summary: A metal-free synthesis of β-carbolines from tryptamines and aromatic aldehydes is achieved using a triaryl carbenium ion pair as a catalyst. This method exhibits excellent functional group tolerance and is demonstrated with the synthesis of Eudistomin U and fluorescent compounds on a large scale. Mechanistic studies reveal the formation of a trityl radical through a single-electron transfer process and its trapping by an oxygen molecule. In addition, an in-situ-generated reactive oxygen-centered radical is found to be essential for the efficient dehydroaromatization process.
CELL REPORTS PHYSICAL SCIENCE
(2023)