Organocatalyzed Kinetic Resolution of Racemic Carboxylic Acids DOI

Ken Okuno,

Yasuaki Furuya,

Seiji Shirakawa

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(1)

Опубликована: Ноя. 1, 2023

Abstract The kinetic resolution of racemic compounds is a reliable method to prepare important chiral molecules in highly optically enriched forms. Although methods for the catalytic alcohols, amines, and epoxides have been extensively investigated, carboxylic acids has remained under‐developed despite importance acids. Excellent approaches via esterification using organocatalysts reported by several research groups. Furthermore, organocatalyzed lactonization alkenyl alkynyl also adapted achieve resolution. Herein, typically used produce are reviewed elucidate current status this research.

Язык: Английский

Chiral sulfide and selenide catalysts for asymmetric halocyclizations and related reactions DOI
Ryuichi Nishiyori,

Taiki Mori,

Ken Okuno

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(16), С. 3263 - 3275

Опубликована: Янв. 1, 2023

Recent advances in chiral sulfide-catalyzed asymmetric halocyclizations are summarized.

Язык: Английский

Процитировано

22

Oxidative Free-Radical C(sp2)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones DOI

Yunhua Xie,

Zhilai Zhang,

Biao Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8521 - 8530

Опубликована: Июнь 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Язык: Английский

Процитировано

6

Recent advances in catalytic asymmetric haloamination and haloetherification of alkenes DOI
Chuan‐Zhi Yao,

Xue‐Qin Tu,

Hua‐Jie Jiang

и другие.

Tetrahedron Letters, Год журнала: 2023, Номер 126, С. 154639 - 154639

Опубликована: Июль 5, 2023

Язык: Английский

Процитировано

11

Recent Advances in Enantioselective Reactions of Terminal Unactivated Alkenes DOI
Qihang Guo,

Xuzhong Shen,

Zhan Lu

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(7), С. 760 - 776

Опубликована: Ноя. 21, 2023

Comprehensive Summary α ‐Olefins as aliphatic terminal alkenes could be obtained easily from numerous contemporary synthetic reactions well petrochemical industry, and also found in natural products. Compared to the attaching directing groups or activating group, catalytic asymmetric reaction of unactivated presents great challenges due weak electron effect small steric hindrance effect. This review mainly summarizes latest progress olefins since 2016. Key Scientists image

Язык: Английский

Процитировано

10

A Theoretical Study on the Mechanism of Bifunctional Brønsted Acid/Base-Catalyzed CO2-Fixation Reaction with Homoallylic Amine DOI
Yu Wang, Xin Zhang, Jia Zhou

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(6), С. 2172 - 2179

Опубликована: Янв. 31, 2025

The reaction mechanism and the enantioselectivity of Brønsted acid/base (trans-stilbene diamine, simplified by BAM)-catalyzed CO2 fixation with homoallylic amine have been investigated using density functional theory (DFT) calculations. proposed involves initial activation acid, followed nucleophilic attack on to form a carbamate intermediate. base subsequently deprotonates intermediate cyclic product, regenerating acid catalyst. C-O cyclization is enantio-determining step. hydrogen bond network formed catalyst substrate, similar an enzyme pocket, plays key role in stereoselectivity. In addition, energy decomposition analysis (EDA) confirms that bonding driven orbital electrostatic attractions. more basic BAM (OMe at quinoline 7-position) exhibits enhanced enantioselectivity.

Язык: Английский

Процитировано

0

Desymmetrizing atroposelective bromination of N-arylcarbazoles enabled by cross-assembled bifunctional catalysts DOI
Jingxian Huang, Hui Yang, Xiao Chen

и другие.

Chem, Год журнала: 2025, Номер unknown, С. 102439 - 102439

Опубликована: Фев. 1, 2025

Язык: Английский

Процитировано

0

Asymmetric Halocyclization of 2-Anilidostyrenes Using N-Haloamides Enabled by Chiral Anion Phase-Transfer Catalysis DOI
Penghui Zhang, Xue Du, Guo-Gang Tu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 31, 2025

Asymmetric halogenation for efficient construction of various 4H-3,1-benzoxazine derivatives with excellent functional group tolerance using readily available N-haloamides as the halogen source and ammonium phosphate salt catalyst under mild reaction conditions has been developed. The loading could be reduced to 1 mol % recycled 4 times without deterioration in reactivity stereoselectivity. Importantly, this process features a column-purification-free operation, leading green atom-economical preparation chiral benzoxazines good yields high enantioselectivities.

Язык: Английский

Процитировано

0

Catalytic Enantioselective Friedel–Crafts Reactions of Arenes Enabled by Iranium/Irenium-Ion-Triggered Electrophilic Functionalization DOI
Yuanyuan Zhang, Shuai Ding,

Limin Meng

и другие.

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Апрель 14, 2025

Abstract The catalytic asymmetric Friedel–Crafts reactions of (hetero)arenes represent a cornerstone in synthetic chemistry due to their ability efficiently incorporate aromatic rings into complex molecular architectures. This account presents comprehensive overview recent advancements the enantioselective (hetero)arenes, with particular focus on that facilitate introduction multiple C–C bonds via iranium/irenium-ion-triggered electrophilic processes. We examine detail strategies and methodologies employed achieve stereoselective incorporation unsaturated bonds, highlighting construction diverse structural scaffolds. Additionally, this showcases broad range applications powerful transformation organic synthesis. 1 Introduction 2 Catalytic Enantioselective Reactions Thiiranium/Thiirenium Ions 2.1 Arylthiiranium/Arylthiirenium-Ion-Triggered 2.2 Trifluoromethylthiiranium/Trifluoromethylthiirenium-Ion-Triggered 3 Haliranium 3.1 Chloriranium-Ion-Triggered 3.2 Bromiranium-Ion-Triggered 3.3 Iodiranium-Ion-Triggered Asymmetric Oxidative Arylation Alkenes 4 Conclusion Outlook

Язык: Английский

Процитировано

0

Asymmetric chloro- and selenocyclization of 2-alkenyl anilides enabled by tertiary ammonium salt catalysis DOI

Xue Du,

Zehua Sun, Penghui Zhang

и другие.

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 111259 - 111259

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0

Catalytic Enantioselective Chlorofunctionalizations of N-Substituted Amides Using In Situ Generated HOCl as Hydrogen Bond Source DOI

Tengbo Ding,

Long Liang, Moucun Yuan

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 29, 2025

Asymmetric organocatalytic halocyclization represents a powerful method for the synthesis of valuable chiral haloheterocycles. However, its heavy dependence on substrates that contain hydrogen bond donors enantiocontrol limits broader application. Here we report catalytic asymmetric chlorofunctionalization olefinic amides do not bear donors, allowing efficient production chlorooxazolidin-2-ones and chloroamino esters featuring quaternary stereocenters, achieved with high yields excellent enantioselectivity. This protocol facilitates N-aryloxazolidin-2-ones establishes useful framework synthesizing antibiotic analogues. Mechanistic studies indicate trace amounts water interact chlorinating agent to produce HOCl in situ, which acts as both proton donor hypochlorite source, thereby promoting cyclization process. strategy significantly broadens potential development diverse array functional molecules.

Язык: Английский

Процитировано

0