Article
Chemistry, Multidisciplinary
Nicole Hanania, Molhm Nassir, Nadim Eghbarieh, Ahmad Masarwa
Summary: We have developed a designed stereodivergent strategy for the synthesis of gem-diborylcyclopropanes, which allows for the highly modular preparation of cyclopropane ring variants with excellent stereocontrol.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Xueying Wang, Yeelin Phang, Jiling Feng, Song Liu, Hong Zhang, Wenwei Fu, Hua Zhou, Gang Xu, Hongxi Xu, Changwu Zheng
Summary: The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. An efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.
Article
Chemistry, Organic
Wenzhe Geng, Hui Wang, Juan Xi, Ruonan Jiang, Jintao Guo, Keqiang Jiao, Mengyao Tang, Qing Liu, Lizhi Zhang, Hui Liu
Summary: A novel and efficient method for the synthesis of polycyclic aromatic compounds has been developed using allenamide and 2-iodoanilines as key building blocks. The cascade cyclization reaction was achieved in one-pot, involving intramolecular cyclization/pi-allylic substitution and intramolecular 6-endo Heck cyclization. This method offers advantages such as readily available substrates, mild conditions, high efficiency, and step economy.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Craig A. Johnston, David B. Cordes, Tomas Lebl, Alexandra M. Z. Slawin, Nicholas J. Westwood
Summary: The study investigates the synthetic route of the bioactive natural product perophoramidine and an alternative N-chlorosuccinimde-mediated reaction for its core structure. Unexpected rearrangement of the core structure was observed during attempts to synthesize the natural product, with X-ray crystallographic analysis providing important analytical confirmation for the assigned structures.
Article
Chemistry, Multidisciplinary
Yicong Luo, Yuqi Ma, Guanlin Li, Xiaohong Huo, Wanbin Zhang
Summary: In this study, a Pd/Cu/Li ternary system has been developed for the stereodivergent synthesis of chiral fluorinated amino acids. By sequential desymmetrization and allylic substitution reactions, non-natural amino acids with excellent selectivity can be synthesized.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lu Wang, Fuxing Shi, Chaorong Qi, Wenjie Xu, Wenfang Xiong, Bangxiong Kang, Huanfeng Jiang
Summary: The study presents a stereodivergent synthesis of beta-iodoenol carbamates through a photocatalytic three-component coupling, demonstrating the potential synthetic utility and practicality of the method. Additionally, this strategy could provide a general method for stereodivergent construction of trisubstituted alkenes, representing a fascinating challenge in the field of organic chemistry research.
Article
Chemistry, Organic
Vunnam Srinivasulu, Gourishetty Srikanth, Monther A. Khanfar, Imad A. Abu-Yousef, Amin F. Majdalawieh, Ralph Mazitschek, Subbaiah Chennam Setty, Anusha Sebastian, Taleb H. Al-Tel
Summary: The complexity-to-diversity (CtD) strategy is a powerful tool for transforming complex natural products into diverse structures. However, existing functional groups often limit the reactions used in this process, restricting access to desired skeletal diversity. By developing stereodivergent strategies, researchers have successfully synthesized diverse natural product-like compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yue Wang, Er-Qing Li, Zheng Duan
Summary: The development of stereodivergent strategies in asymmetric synthesis is crucial for accessing the full range of stereoisomers in products with multiple stereocenters. In this study, a novel P-chirogenic ligand, YuePhos, was developed to achieve precise switching of product stereochemistry in a Pd-catalyzed asymmetric cycloaddition reaction. The method provides an efficient route for the synthesis of pyrrolidines with up to three adjacent stereocenters, with excellent enantiomeric excesses.
Article
Chemistry, Multidisciplinary
Byungjun Kim, Yuna Song, Sarah Yunmi Lee
Summary: In this study, a silver-catalyzed method was developed for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. By utilizing catalyst control and stereospecificity, all four product stereoisomers containing two adjacent stereocenters can be accessed with high stereoselectivity.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Bo Yang, Xingfa Tan, Yicong Ge, Yingzi Li, Chuan He
Summary: In this study, an efficient one-pot strategy for the stereodivergent asymmetric synthesis of various P-atropisomeric Si-stereogenic monohydrosilanes with excellent stereoselectivity was developed. This method provides an effective platform for the synthesis of enantioenriched phosphine-based silicon-stereogenic monohydrosilanes, which could have potential applications in asymmetric catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Bo Yang, Xingfa Tan, Yicong Ge, Yingzi Li, Chuan He
Summary: Silicon-stereogenic monohydrosilanes have broad applications, but their combination with phosphines is rare. In this study, an efficient one-pot strategy was developed for the asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes, which have potential applications in asymmetric catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Computer Science, Artificial Intelligence
Eran Dahan, Yosi Keller
Summary: This work proposes a deep learning-based approach for kin verification with a unified multi-task learning scheme, effectively utilizing small training sets. It introduces a novel method for fusing kin images embeddings and an adaptive sampling scheme to address the imbalance in datasets. Experimental results demonstrate its superiority over contemporary state-of-the-art kin verification results on various datasets.
IEEE TRANSACTIONS ON PATTERN ANALYSIS AND MACHINE INTELLIGENCE
(2021)
Article
Computer Science, Artificial Intelligence
Alaa Maalouf, Gilad Eini, Ben Mussay, Dan Feldman, Margarita Osadchy
Summary: The limitation of coresets in practical applications has led to the proposal of a learning-based algorithm for their construction, which has shown to yield better results in experiments. This new approach offers a solution to the limitations of traditional coresets.
IEEE TRANSACTIONS ON NEURAL NETWORKS AND LEARNING SYSTEMS
(2022)
Article
Chemistry, Organic
Ryota Sakamoto, Minami Odagi, Atsuto Izumiseki, Kaname Konuki, Kazuo Nagasawa
Summary: In this study, we describe a versatile method for the synthesis of homoallenylboronic esters via lithiation-borylation and subsequent 1,2-rearrangement. The resulting homoallenylboronic esters can be successfully converted into Z- and E-1,3-dienes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Fangyuan Wang, Zongpeng Zhang, Yu Chen, Virginie Ratovelomanana-Vidal, Peiyuan Yu, Gen-Qiang Chen, Xumu Zhang
Summary: In this study, a method for synthesizing 3,4-disubstituted succinimides is reported, and the origin of stereoselectivity is elucidated through experimental and theoretical investigations. The method exhibits high catalytic activity and stereoselectivity, and different configurations of products can be obtained by controlling reaction conditions. This study provides a straightforward and stereodivergent approach for synthesizing enantioenriched succinimides of significant enzymatic selectivity from inexpensive chemical feedstocks in a single reaction step.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Jiun-Le Shih, Po-An Chen, Jeremy A. May
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Truong N. Nguyen, Thien S. Nguyen, Jeremy A. May
Article
Chemistry, Organic
Santa Jansone-Popova, Jeremy A. May
Review
Chemistry, Organic
Po-An Chen, Jeremy A. May
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Truong N. Nguyen, Jeremy A. May
Article
Chemistry, Inorganic & Nuclear
Hiroyuki Hattori, Dong Hyun Koo, Jeremy A. May
Article
Chemistry, Organic
Jeremy A. May, Thien S. Nguyen, Truong N. Nguyen, Phong Q. Le, Po-An Chen, Ravikrishna Vallakati
Article
Chemistry, Organic
Truong N. Nguyen, Jeremy A. May
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Multidisciplinary
Jiun-Le Shih, Santa Jansone-Popova, Christopher Huynh, Jeremy A. May
Article
Chemistry, Organic
Truong N. Nguyen, Jeremy A. May
Review
Biochemistry & Molecular Biology
Truong N. Nguyen, Po-An Chen, Krit Setthakarn, Jeremy A. May
Article
Chemistry, Organic
Qinxuan Wang, Jeremy A. May
Article
Chemistry, Organic
Qinxuan Wang, Jiun-Le Shih, Ka Yi Tsui, Croix J. Laconsay, Dean J. Tantillo, Jeremy A. May
Summary: This study investigated various types of Huisgen cyclization or nitrene/carbene alkyne cascade reactions with different types of termination. Accessible nitrene precursors were evaluated, and carbonazidates were found to be the only effective initiators. The reaction outcome can be influenced by solvents, terminal alkynyl substituents, and catalysts. The mechanism was studied both computationally (using density functional theory) and experimentally, revealing relevant intermediates and plausible reaction pathways.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Clayton P. Donald, Amy Boylan, Truong N. Nguyen, Po-An Chen, Jeremy A. May
Summary: The (IPr)GaCl3/AgSbF6, AgSbF6, and GaCl3 catalysts were found to efficiently catalyze the substitution of the hydroxyl group of secondary and tertiary propargylic alcohols with organoboronic acids via C-C bond formation, and GaCl3 catalyst effectively synthesized all-carbon quaternary propargylic centers. These catalysts demonstrated the ability to perform substitutions at carbons bearing alkyl substituents, a capability that was lacking in other systems. The study showed that highly hindered carbon stereocenters, including quaternary centers bearing doubly ortho-substituted aryl rings, could be accessed efficiently using this method.
Article
Chemistry, Organic
Jirong Luo, Jeremy A. May
Summary: Cannabinoid research relies on synthesizing derivatives for structure-activity relationship studies. (-)-Delta(9)- Tetrahydrocannabinol and cannabidiol were successfully synthesized via a seven-step reaction using a novel ambiphilic trifluoroborate in a tandem enantioselective conjugate addition/enolate alkylation annulation. A new class of alkenyl and aryl ambiphilic trifluoroborates were also synthesized, demonstrating great compatibility with various functional groups, high yields, and excellent enantio- and diastereoselectivity. Furthermore, a novel benzo-fused cannabinoid analogue and tandem quaternary stereocenter-containing reaction products were synthesized with good to excellent enantioselectivity.