Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Allwin D. McDonald, Samantha K. Bruffy, Aadhishre T. Kasat, Andrew R. Buller
Summary: In this study, we used a substrate multiplexed screening approach to improve the substrate scope overlap in biocatalytic cascades for the synthesis of chiral 1,2-amino alcohols. By engineering the activity of enzymes, we achieved selective and efficient synthesis of enantiopure products in a one-pot cascade reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Changpeng Chen, Wenqing Guo, Deyong Qiao, Shaolin Zhu
Summary: We report a NiH-catalyzed asymmetric migratory hydroalkylation process for the efficient and selective construction of enantioenriched multi-substituted cycloalkanes. Through a dynamic kinetic asymmetric transformation (DYKAT), easily accessible racemic and isomeric mixtures of cycloalkenes could be directly utilized as starting materials, convergently producing highly regio-, diastereo-, and enantioselective chiral 1,2-cis disubstituted cycloalkanes. In addition, prochiral cyclic alkenes can also be employed, delivering chiral 1,2-cis disubstituted cycloalkanes through desymmetrization process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Marina Velado, Manuel Martinovic, Ines Alonso, Mariola Tortosa, Roberto Fernandez de la Pradilla, Alma Viso
Summary: The base-induced [2,3]-sigmatropic rearrangement of enantiopure 2-sulfinyl dienes has been optimized using NaH and iPrOH. The reaction proceeds through allylic deprotonation and sulfoxide-sulfenate rearrangement. The presence of a terminal allylic alcohol is crucial for achieving complete regioselectivity and high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Lyazid Ait Said, Mohamed Merouane El Hammoumi, Chaimaa El Haimer, Abdelhadi El Bachiri, Mostafa Khoukhi
Summary: Two new compounds of beta-amino alcohol were synthesized using (R)-(+)-alpha-methylbenzylamine as the starting material, and these compounds were found to react with a 1:1 mixture of cis and trans-limonene oxide in the presence of water, yielding beta-amino alcohols and unreacted limonene oxides or amines in the products.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Xiaolei Li, Jicheng Wu, Weiping Tang
Summary: Human glycans are mainly composed of nine common sugar building blocks, while hundreds of different monosaccharides have been found in bacteria. A new efficient strategy has been developed to access rare sugars from common monosaccharides, which can be used for constructing glycoside skeletons in natural products or bioactive compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Applied
Viacheslav V. Pendiukh, Hanna V. Yakovleva, Ivan A. Stadniy, Alexander E. Pashenko, Eduard B. Rusanov, Natalia V. Grabovaya, Sergey V. Kolotilov, Alexander B. Rozhenko, Serhiy V. Ryabukhin, Dmytro M. Volochnyuk
Summary: A novel approach for safe generation of diazomethane-contained organic solution was proposed using a serial flow reactor. Chiral diazoketones were prepared through the reaction of diazomethane with mixed anhydrides, and exhibited good stability and applicability.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Multidisciplinary
Xin Chang, Xiang Cheng, Chun-Jiang Wang
Summary: This article introduces an efficient method for synthesizing pharmaceutical compounds with deuterium labels, which addresses the challenge of building deuterium-containing stereogenic centers in organic synthesis. By combining H/D exchange and 1,3-dipolar cycloaddition in a catalytic asymmetric strategy, bioactive alpha-deuterated pyrrolidine derivatives were constructed with high yields and excellent stereoselectivities.
Article
Chemistry, Organic
Travis Menard, Aragorn Laverny, Scott E. Denmark
Summary: This method describes the catalytic, enantioselective carbosulfenylation of alkenes to construct difficult-to-generate, enantioenriched, 3,4-disubstituted chromans with moderate to high yields and excellent enantioselectivities. The resulting thioether moiety is amenable to various functional group manipulations and transformations, providing access to sulfur-containing functional groups present in natural products and pharmaceuticals.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Will C. Hartley, Florian Schiel, Elena Ermini, Paolo Melchiorre
Summary: We reported a catalytic asymmetric protocol for preparing chiral pyrrolidinones via a radical pathway. This chemistry combines photoredox catalysis and Lewis base catalysis to achieve the first example of asymmetric radical conjugate addition to alpha,beta-unsaturated anhydrides and esters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jichao Chen, Evangelos Miliordos, Ming Chen
Summary: A Cu-catalyzed carboboration reaction was developed to generate enantioenriched 3,6'-bisboryl-anti-1,2-oxaborinan-3-enes. DFT calculations revealed the formation of a stable (3)eta-allylic copper intermediate during the initial diene 1,2-borocupration. The subsequent aldehyde addition proceeded under Curtin-Hammett control to provide products with high enantioselectivities, with the three boryl groups in the products properly differentiated for further transformations into enantioenriched homoallylic alcohols with a stereodefined trisubstituted alkene.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tianyi Zheng, Janna L. Berman, Forrest E. Michael
Summary: In this study, a diastereoconvergent synthesis of anti-1,2-amino alcohols bearing N-containing quaternary stereocenters was reported. By destroying the allylic stereocenter, a single diastereomer of the product can be selectively formed from any diastereomeric mixture of the starting homoallylic alcohol derivatives, eliminating the need for diastereoselective preparation of starting materials.
Article
Chemistry, Organic
Zachary P. Sercel, Alexander W. Sun, Brian M. Stoltz
Summary: Enantioenriched gem-disubstituted 4-imidazolidinones were prepared in high yield and high enantioselectivity through Pd-catalyzed decarboxylative asymmetric allylic alkylation. A rapid synthetic route starting from 2-thiohydantoin was developed, and the orthogonality of the protecting groups used for nitrogen-rich products was demonstrated, indicating potential applications in drug design.
Article
Chemistry, Multidisciplinary
Yu Li, Na Hu, Zefei Xu, Yunfeng Cui, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu, Yanhe Ma
Summary: The enzymatic asymmetric reductive amination process can be used to convert simple aldehydes and amines into chiral N-substituted 1,2-amino alcohols, providing an environmentally friendly and economical method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xin Liu, Lukman O. Alimi, Niveen M. Khashab
Summary: An intrinsically porous triazene macrocycle is reported to selectively separate cis-1,2-dichloroethene from a mixture of cis- and trans-DCE with a purity of over 96% through enhanced host/guest C-H...pi intermolecular interactions. The macrocycle can be reused multiple times without any decrease in performance, supporting the sustainability of using molecular sieves in chemical separation.
CHEMICAL COMMUNICATIONS
(2022)
