Article
Chemistry, Organic
Rui-Han Dai, Qi Wang, Zhi-Xiong Chen, Shi-Kai Tian
Summary: An unprecedented asymmetric aza-Claisen rearrangement was discovered to proceed without catalysts and additives, providing easy access to structurally diverse delta-chiral beta-diketones with high yields and excellent retention of enantiopurity. This protocol proved powerful for the construction of an all-carbon quaternary stereocenter with high enantiopurity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Soo Min Cho, Si Yeon Lee, Do Hyun Ryu
Summary: A catalytic enantioselective acyloin rearrangement is utilized to synthesize highly optically active acyloin derivatives, yielding chiral alpha-hydroxy aryl ketones and chiral alpha-siloxy alkyl ketones with high yields and good enantioselectivity.
Article
Chemistry, Multidisciplinary
Yennie H. Nguyen, Vinh Q. Dang, Joao Vitor Soares, Judy I. Wu, Thomas S. Teets
Summary: The lack of efficient and robust deep-blue phosphorescent metal complexes is a major challenge in electroluminescent color displays. Increasing the s-donating ability of the ligands can ameliorate the deactivation of blue phosphors by low-lying metal-centered states. We have revealed a synthetic strategy to access blue-phosphorescent complexes using two supporting acyclic diaminocarbenes (ADCs), which are stronger s-donors than N-heterocyclic carbenes (NHCs). These new platinum complexes have excellent photoluminescence quantum yields, with four out of six complexes exhibiting deep-blue emission. Experimental and computational analyses confirm the destabilization of the (MC)-M-3 states by the ADCs.
Article
Chemistry, Inorganic & Nuclear
Svetlana A. Katkova, Daria O. Kozina, Kristina S. Kisel, Maria A. Sandzhieva, Dmitriy A. Tarvanen, Sergey V. Makarov, Vitaly V. Porsev, Sergey P. Tunik, Mikhail A. Kinzhalov
Summary: A series of cyclometalated platinum(ii) complexes with acyclic diaminocarbene (ADC) ancillary ligands were designed and synthesized. Their photophysical properties were investigated both experimentally and theoretically. The complexes showed green phosphorescence with high quantum efficiency of up to 45% in 2 wt% doped PMMA film at room temperature. These complexes were further utilized as light-emitting dopants for OLED fabrication. The resulting devices demonstrated green emission with a maximum current efficiency of 2.9 cd A(-1) and a luminance of 2700 cd m(-2), highlighting the potential of these cyclometalated platinum(ii) complexes as efficient green emitters for OLED devices.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Subhadip De, Breanna M. Tomiczek, Yinuo Yang, Kenneth Ko, Ion Ghiviriga, Adrian Roitberg, Alexander J. Grenning
Summary: In this study, a diastereoselective indole-dearomative Cope rearrangement is reported. The reaction is driven by multiple minor forces, leading to the successful assembly of structurally complex products with vicinal stereocenters and diverse functional groups for further transformations.
Article
Chemistry, Organic
Qi Xiong, Lu Xiao, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, an iridium-catalyzed cascade allylation/macrolactonization reaction was developed, which efficiently synthesizes chiral macrodiolides with excellent diastereoselectivities and enantioselectivities. This method is characterized by readily available substrates, high stereoselective control, and efficient synthetic steps.
Article
Chemistry, Multidisciplinary
Junqiang Wei, Vincent Gandon, Ye Zhu
Summary: Synthetic application of asymmetric catalysis requires strategic alignment of bond construction and chiral target molecule creation. Remote desymmetrization offers advantages in spatial decoupling of catalytic transformation and generation of stereogenic element. However, this spatial separation presents challenges for chiral catalysts to discriminate distant enantiotopic sites several bonds away from a prochirality center.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Mo Wang, Zhenfeng Zhang, Wanbin Zhang
Summary: This article introduces the development of chiral bicyclic imidazole catalysts by our research group, including their design, synthesis, and application. By using different skeletons and substituents, a series of highly active and selective catalysts were successfully prepared and applied in asymmetric synthesis reactions. This research provides important insights and guidance for exploring new organocatalysts and related reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Applied
Yusuke Oyamada, Shintaro Yamasaki, Mika Tsuzuki, Takumi Kitagawa, Masaru Kondo, Takahiro Sasamori, Shuichi Nakamura
Summary: The catalytic enantioselective allenylation of ketimines derived from isatins is reported. High regio- and enantioselective products were obtained using a bis(imidazoline)-palladium catalyst. The obtained products were further converted into various chiral amines. The stereoselectivity origin was revealed by DFT calculations of the transition state.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Joshua A. Malone, Satish Chandra Philkhana, Jacob R. Stepherson, Fatimat O. Badmus, Frank R. Fronczek, Rendy Kartika
Summary: This article describes a new synthetic reaction that can generate all-carbon bisquaternary centers at the opposing side of alpha-carbons in cyclohexanone with four different substituents in a controlled manner.
Article
Chemistry, Applied
Wei-Jung Chiu, Jin-Yu Chen, Shih- Liu, Indrajeet J. Barve, Wan-Wen Huang, Chung-Ming Sun
Summary: A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from alpha-amino acid esters and 2-alkynyl benzaldehydes is reported. The strategy involves an unconventional Pictet-Spengler reaction and subsequent gold-catalyzed intramolecular hydroamination. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Dongxu He, Chen Xu, Xiangyou Xing
Summary: This manuscript presents a study on asymmetric transfer hydrogenation using Ru-based catalysts. By employing Ru-catalysts with minimal stereo-genicity in combination with formic acid/triethylamine as the hydrogen donor, efficient synthesis of N-diphenylphosphinyl acyclic imines was achieved. The catalytic system was compatible with various aryl alkyl and heteroaryl alkyl substituted imines, resulting in reduced amines with excellent enantiomeric excess and yields.
Article
Chemistry, Multidisciplinary
Lu Han, Sheng-Jun Li, Xue-Ting Zhang, Shi-Kai Tian
Summary: The study presents an unprecedented aromatic aza-Claisen rearrangement reaction, converting arylpropargylammonium salts into 2-propargylanilines with moderate to good yields and high regioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Ruiqi Tong, Song Liu, Chen Zhao, Dongyang Jiang, Lu Gao, Wanshu Wang, Bengui Ye, Zhenlei Song
Summary: A new nonracemic reagent has been developed for the asymmetric crotylboration of aldehydes. This reaction provides compounds with high yields and excellent stereo-selectivity, showcasing its potential in the synthesis of polyketide natural products.
Article
Biochemistry & Molecular Biology
Christian Schumacher, Lieselotte Fritz, Lena M. M. Hanek, Vitali Sidorin, Daniel Bruex, Carsten Bolm
Summary: This study presents the development of a mechanochemical protocol for a charge-accelerated aza-Claisen rearrangement, which avoids the use of transition metals, ligands, or pyrophoric Lewis acids. The desired tertiary amides were prepared in yields ranging from 17% to 84% by using (heterocyclic) tertiary allylamines and acyl chlorides. Furthermore, the same protocol was applied for a Bellus-Claisen-type rearrangement resulting in the synthesis of a 9-membered lactam without further optimization.
Article
Chemistry, Multidisciplinary
Dipesh Prema, Yohan L. N. Mathota Arachchige, Rex E. Murray, LeGrande M. Slaughter
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Organic
Sachin Handa, Sri S. Subramanium, Aaron A. Ruch, Joseph M. Tanski, LeGrande M. Slaughter
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Aaron A. Ruch, Fanji Kong, Vladimir N. Nesterov, LeGrande M. Slaughter
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Organic
Aaron A. Ruch, Sachin Handa, Fanji Kong, Vladimir N. Nesterov, Dale R. Pahls, Thomas R. Cundari, LeGrande M. Slaughter
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Biochemical Research Methods
Pavel Majek, Jan Krupcik, Zachary S. Breitbach, Milan K. Dissanayake, Peter Kroll, Aaron A. Ruch, LeGrande M. Slaughter, Daniel W. Armstrong
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
(2017)
Article
Biochemical Research Methods
Yasith S. Nanayakkara, Ross M. Woods, Zachary S. Breitbach, Sachin Handa, LeGrande M. Slaughter, Daniel W. Armstrong
JOURNAL OF CHROMATOGRAPHY A
(2013)
Article
Chemistry, Inorganic & Nuclear
Aaron A. Ruch, Matthew C. Ellison, John K. Nguyen, Fanji Kong, Sachin Handa, Vladimir N. Nesterov, LeGrande M. Slaughter
Summary: The study synthesized sterically encumbered gold(I) acyclic diaminocarbene (ADC) complexes with different ligands and found that the bulky biaryl/terphenyl groups strongly influence product selectivity in gold-catalyzed reactions. The research also revealed how large aryl groups impact reaction mechanisms.
Meeting Abstract
Chemistry, Multidisciplinary
Aaron Ruch, John Nguyen, Matthew Ellison, LeGrande Slaughter
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Meeting Abstract
Chemistry, Multidisciplinary
Aaron Ruch, Vladimir Nesterov, LeGrande Slaughter
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Meeting Abstract
Chemistry, Multidisciplinary
Aaron Ruch, LeGrande Slaughter, Fanji Kong, Vladimir Nesterov
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Meeting Abstract
Chemistry, Multidisciplinary
Aaron Ruch, Xiaofan Zhang, Fanji Kong, LeGrande Slaughter
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Meeting Abstract
Chemistry, Multidisciplinary
LeGrande Slaughter, Aaron Ruch, Sachin Handa
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Meeting Abstract
Chemistry, Multidisciplinary
Yohan L. N. Mathota Arachchige, James Le, LeGrande M. Slaughter
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Meeting Abstract
Chemistry, Multidisciplinary
LeGrande M. Slaughter, Sachin Handa, Aaron A. Ruch
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Meeting Abstract
Chemistry, Multidisciplinary
Aaron Ruch, Legrande Slaughter
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
