Diastereodivergence in catalytic asymmetric conjugate addition of carbon nucleophiles DOI
Byungjun Kim,

Hooseung Lee,

In‐Sun Song

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер unknown

Опубликована: Дек. 11, 2024

Catalytic asymmetric conjugate additions of carbon nucleophiles have emerged as a potent tool for constructing multi-stereogenic molecules with precise stereochemical control. This review explores the concept diastereodivergence in such reactions, focusing on strategies to achieve selective access diverse diastereomeric products upon carbon-carbon bond formation. Drawing from rich array examples, we delve into key approaches controlling outcome these transformations, including alteration alkene geometry, fine-tuning reaction parameters, synergistic catalysis, and isomerization adducts. Additionally, highlight iterative additions, showcasing their potential diastereodivergent synthesis methyl-branched stereocenters 1,3-relationships. By presenting concentrated overview this significant topic, aims provide valuable insights design execution stereodivergent catalytic offering new avenues advancing stereoselective structural diversity organic synthesis.

Язык: Английский

Synergistic Dual Catalysis in Stereodivergent Synthesis DOI
Liang Wei, Cong Fu,

Zuo-Fei Wang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(6), С. 3812 - 3844

Опубликована: Фев. 23, 2024

Chiral skeletons with multiple stereogenic centers widely reside in nature and drugs, their relative absolute configuration often determine physiological or pharmacological properties. Stereodivergent synthesis of chiral molecules is not only great significance, but also highly challenging since the formation one diastereomers inherently preferred most asymmetric reactions. dual catalysis, introduced 2013 by Carreira group, perfectly catered to all requirements for full stereoselectivity control given reactions two catalysts are utilized a synergistic way act independently, has now been arguably efficient strategy realize stereodivergent synthesis. This comprehensive review presents an overview development enabled catalysis past ten years, providing readers fundamental attributes as well ability, scope, mechanism, limitations this strategy.

Язык: Английский

Процитировано

31
Recent advances in Stereoselective Construction of Fluorinated Quaternary Carbon Centers from Fluorinated Compounds DOI

Zongwei Li,

Lin Fan,

Guodu Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(23), С. 4592 - 4612

Опубликована: Янв. 1, 2024

Synthesis of fluorinated quaternary carbon centers by a series asymmetric alkylation, arylation, Mannich, Michael addition, aldol, and allylation reactions.

Язык: Английский

Процитировано

5
Borane-Catalyzed Enantioselective α-Alkylation of Unactivated 2-Alkylbenzoxazoles with Electron-Deficient Olefins DOI

Chongren Ai,

Lu Liu, Xiaochen Wang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(35), С. 24663 - 24669

Опубликована: Авг. 20, 2024

Chiral borane–catalyzed reactions have recently emerged as a powerful tool for the enantioselective production of chiral scaffolds. In this study, we demonstrated first time that bisborane catalyst can be used α-functionalization 2-alkylazaarenes; specifically, accomplished unprecedented highly α-alkylation unactivated 2-alkylbenzoxazoles with electron-deficient olefins. The strong Lewis acidity and steric bulk were essential to observed reactivity selectivity.

Язык: Английский

Процитировано

5
Stereodivergent Carbon–Carbon Bond-Forming Reactions DOI
Alan R. Healy

Synthesis, Год журнала: 2024, Номер 56(14), С. 2223 - 2233

Опубликована: Янв. 29, 2024

Abstract Stereodivergent catalysis has emerged as a compelling strategy for achieving stereochemical diversity in small-molecule library design and natural product synthesis. In this short review, key examples of pioneering catalytic carbon–carbon bond-forming transformations that provide access to all stereoisomers given are presented. Current trends future directions the field discussed, highlighting ongoing initiatives enhance efficiency broaden scope stereodivergent methodologies. 1 Introduction 2 Mono-catalysis 2.1 Change Reaction Conditions 2.2 Catalyst 3 Multi-catalysis 3.1 Bifunctional Catalysis 3.2 Sequential/Cascade 3.3 Synergistic/Cooperative 4 Conclusions Outlook

Язык: Английский

Процитировано

4
Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide DOI Creative Commons

Hao-Chen Wen,

Wei Chen, Meng Li

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июнь 20, 2024

The synthesis of chiral α-azaheteroaryl oxiranes via enantioselective catalysis is a formidable challenge due to the required complex stereoselectivity and diverse N-heterocyclic structures. These compounds play crucial role in developing bioactive molecules, where precise chirality significantly influences biological activity. Here we show that using phosphoric acid as catalyst, our method efficiently addresses these challenges. This technique not only achieves high enantio- diastereoselectivity but also demonstrates superior chemo- stereocontrol during epoxidation alkenyl aza-heteroarenes. Our approach leverages synergistic blend electrostatic hydrogen-bonding interactions, enabling effective activation both substrates hydrogen peroxide. resulting exhibit enhanced diversity functionality, aiding construction azaaryl with contiguous stereocenters. Kinetic density functional theory studies elucidate mechanism, highlighting acid's pivotal this intricate process.

Язык: Английский

Процитировано

4
3-Alkyl-1,2,4-triazines as Heterocyclic Platforms for Organocatalytic Enantioselective Benzylic C–H Functionalization DOI
Anthony Lapray, Marie‐Aude Hiebel, Sylvain Oudeyer

и другие.

Organic Letters, Год журнала: 2025, Номер 27(6), С. 1504 - 1510

Опубликована: Янв. 31, 2025

The α-3-(1,2,4-triazine)-α-cyanoacetate derivatives exhibit a unique and well-defined dearomatized structure undergoing efficient organocatalytic aromatization–alkylation sequences with Michael acceptors in order to construct an all-carbon tetrasubstituted stereocenter high ee values. These new players the field of enantioselective catalytic benzylic C–H functionalization afford versatile molecular platforms toward construction valuable 3D-heterocycles.

Язык: Английский

Процитировано

0
Ni/Cu Dual‐Catalyzed Propargylation for the Stereodivergent Synthesis of Methohexital DOI Creative Commons
Xihao Chang, Jiayin Zhang, Xiang Cheng

и другие.

Advanced Science, Год журнала: 2024, Номер unknown

Опубликована: Июль 25, 2024

The development of efficient methodologies for the controlled manufacture specific stereoisomers bearing quaternary stereocenters has prompted advances in a variety scientific disciplines including pharmaceutical chemistry, materials science, and chemical biology. However, complete control absolute relative stereochemical configurations alkyne derivatives remains an unmet synthetic challenge. Herein, Ni/Cu dual-catalyzed asymmetric propargylic substitution reaction is presented to produce propargylated products with all-carbon high yields significant diastereo- enantioselectivities (up >20:1 dr, >99% ee). synthesis all variants methohexital, widely used sedative-hypnotic drug, exemplifies efficacy stereodivergent propargylation.

Язык: Английский

Процитировано

2
Stereodivergent dual catalysis in organic synthesis DOI

Hong Sun,

Yue Ma,

Guorong Xiao

и другие.

Trends in Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 1, 2024

Язык: Английский

Процитировано

2
Recent Progress in Synthesis of Alkyl Fluorinated Compounds with Multiple Contiguous Stereogenic Centers DOI Creative Commons
Xuemei Yin, Xihong Wang, Lei Song

и другие.

Molecules, Год журнала: 2024, Номер 29(15), С. 3677 - 3677

Опубликована: Авг. 2, 2024

Organic fluorides are widely used in pharmaceuticals, agrochemicals, material sciences, and other fields due to the special physical chemical properties of fluorine atoms. The synthesis alkyl fluorinated compounds bearing multiple contiguous stereogenic centers is most challenging research area synthetic chemistry has received extensive attention from chemists. This review summarized important progress field over past decade, including asymmetric electrophilic fluorination elaboration substrates (such as allylic alkylation reactions, hydrofunctionalization Mannich addition Michael aldol miscellaneous reactions), with an emphasis on methodologies, substrate scopes, reaction mechanisms.

Язык: Английский

Процитировано

1
Recent Advances in Nonprecious Metal Catalysis DOI
Archita Sripada, Eugene Chong, Hao Wu

и другие.

Organic Process Research & Development, Год журнала: 2024, Номер 28(9), С. 3524 - 3544

Опубликована: Авг. 9, 2024

Developing catalytic reactions using nonprecious-metal to achieve various synthetic transformations remains a valuable pursuit the scientific community. As part of continuing review series that is published within precompetitive chemistry alliance between AbbVie, Boehringer Ingelheim and Pfizer, this article underscores wide-ranging uses Cu-, Co-, Fe-, Ni-catalysis. The significant uptick in NPMC-related publications signifies escalating curiosity among researchers investigate advance capabilities these metals.

Язык: Английский

Процитировано

1