Meng‐Lan Shen

Anhui Agricultural University

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Pu‐Sheng Wang

Hefei National Center for Physical Sciences at Nanoscale

Liu‐Zhu Gong

Hefei National Center for Physical Sciences at Nanoscale

Chuan‐Zhi Yao

Anhui Agricultural University

Jie Yu

Anhui Agricultural University

Fang Wei

Anhui Agricultural University

Hua‐Jie Jiang

Anhui Agricultural University

Qiankun Li

Anhui Agricultural University

Zhenhua Gu

University of Science and Technology of China

Z. Y. Pei

Guangzhou University

Yan-Dong Meng

Anhui Agricultural University

Cooperative Institutions

Anhui Agricultural University

University of Science and Technology of China

Hefei National Center for Physical Sciences at Nanoscale

Hefei University

Chinese Academy of Sciences

Southern University of Science and Technology

Collaborative Innovation Center of Chemical Science and Engineering Tianjin

Zhejiang University

Center for Excellence in Molecular Cell Science

State Key Laboratory of Clean Energy Utilization

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Unlocking Chiral Sulfinimidoyl Electrophiles: Asymmetric Synthesis of Sulfinamides Catalyzed by Anionic Stereogenic-at-Cobalt(III) Complexes

Journal of the American Chemical Society (2025)

Hua‐Jie Jiang Fang Wei Xingfeng Chen Xin-Ran Yu Yan-Dong Meng

Asymmetric catalysis involving a sulfoxide electrophile intermediate presents an efficient methodology for accessing stereogenic-at-sulfur compounds, such as sulfinate esters, sulfinamides, etc., which have garnered increasing attention in modern pharmaceutical sciences. However, as the aza-analog of sulfoxide electrophiles, the asymmetric issues about electrophilic sulfinimidoyl species remain largely unexplored and represent a significant challenge in sulfur stereochemistry. Herein, we exhibit an anionic stereogenic-at-cobalt(III) complex-catalyzed asymmetric synthesis of chiral sulfinamides via chiral sulfinimidoyl iodide intermediates. Mechanistic investigations reveal that the catalytic cycle is initiated by asymmetric oxidative iodination, generating sulfinimidoyl iodides. These active intermediates subsequently undergo an enantiospecific nucleophilic substitution with water, affording a diverse array of enantioenriched sulfinamides. Notably, these sulfinamides exhibit promising antifungal activities against Sclerotinia sclerotiorum and serve as ideal platform molecules facilitating the stereospecific transformation into various stereogenic aza-sulfur compounds.

Stereocenter

10.1021/jacs.4c16233

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Counteranion-controlled regioselectivity in palladium-catalyzed allylic amination of dienyl allylic carbonates

Tetrahedron (2021)

Meng‐Lan Shen Pu‐Sheng Wang Liu‐Zhu Gong

Phosphoramidite

10.1016/j.tet.2021.131996

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Citations (10)

Transition-Metal-Catalyzed Asymmetric Allylation of Carbonyl Compounds with Unsaturated Hydrocarbons

Synthesis (2017)

Liu‐Zhu Gong Pu‐Sheng Wang Meng‐Lan Shen

The asymmetric allylation of carbonyl compounds is an important process for the formation of carbon–carbon bonds, generating optically active homoallylic alcohols that are versatile building blocks with widespread applications in organic synthesis. The use of readily available unsaturated hydrocarbons as allylating reagents in the transition-metal-catalyzed asymmetric allylation has received increasing interest as either a step- or an atom-economy alternative. This review summarizes transition-metal-catalyzed enantioselective allylations on the basis of the ‘indirect’ and ‘direct’ use of simple unsaturated hydrocarbons (include dienes, allenes, alkynes, and alkenes) as allylating reagents, with emphasis on highlighting conceptually novel reactions. 1 Introduction 2 ‘Indirect’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds 2.1 Enantioselective Allylation with 1,3-Dienes 2.2 Enantioselective Allylation with Allenes 2.3 Enantioselective Allylation with Alkenes 3 ‘Direct’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds 3.1 Enantioselective Allylation with 1,3-Dienes 3.2 Enantioselective Allylation with Allenes 3.3 Enantioselective Allylation with Alkynes 3.4 Enantioselective Allylation with Alkenes 4 Conclusions

10.1055/s-0036-1590986

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Citations (44)

Palladium‐Catalyzed Branch‐ and Z‐Selective Allylic C−H Amination with Aromatic Amines

Angewandte Chemie (2022)

Rui Liu Meng‐Lan Shen Lian‐Feng Fan Xiao‐Le Zhou Pu‐Sheng Wang

Abstract Allylamines are important building blocks in the synthesis of bioactive compounds. The direct coupling of allylic C−H bonds and commonly available amines is a major synthetic challenge. An allylic C−H amination of 1,4‐dienes has been accomplished by palladium catalysis. With aromatic amines, branch‐selective allylic aminations are favored to generate thermodynamically unstable Z‐allylamines. In addition, more basic aliphatic cyclic amines can also engage in the reaction, but linear dienyl allylic amines are the major products.

10.1002/ange.202211631

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Asymmetric S‐Arylation of Sulfenamides to Access Axially Chiral Sulfilimines Enabled by Anionic Stereogenic‐at‐Cobalt(III) Complexes

Angewandte Chemie International Edition (2024)

Hua‐Jie Jiang Fang Wei Yonggang Meng Shu-Ying Ding Jian‐Zhong Wang

An efficient enantioselective coupling reaction between sulfenamides and cyclic diaryliodonium salts is established via adaptive Cu/anionic stereogenic‐at‐Co(III) complex combined catalysis, precisely synthesizing a broad range of axially chiral sulfilimines with excellent enantioselectivities, diastereoselectivities, regioselectivities, and chemoselectivities (67 examples under same conditions, up to 98% ee). The following thermodynamically controlled pyramidal inversion enables efficient stereodivegent synthesis of all four stereoisomers. Mechanistic studies suggest that anionic stereogenic‐at‐cobalt(III) complexes serve as counteranions of diaryliodonium and anionic ligand of Cu(I) catalyst simultaneously, which could be regarded as an explanation for outstanding selectivities.

Stereocenter

10.1002/anie.202419596

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Access to Chiral Hydropyrimidines through Palladium‐Catalyzed Asymmetric Allylic C−H Amination

Angewandte Chemie International Edition (2017)

Pu‐Sheng Wang Meng‐Lan Shen Tian‐Ci Wang Hua‐Chen Lin Liu‐Zhu Gong

Abstract A palladium‐catalyzed asymmetric intramolecular allylic C−H amination controlled by a chiral phosphoramidite ligand was established for the preparation of various substituted chiral hydropyrimidinones, the precursors of hydropyrimidines, in high yields with high enantioselectivities. In particular, dienyl sodium N ‐sulfonyl amides bearing an arylethene‐1‐sulfonyl group underwent a sequential allylic C−H amination and intramolecular Diels–Alder (IMDA) reaction to produce chiral fused tricyclic tetrahydropyrimidinone frameworks in high yields and with high levels of stereoselectivity. Significantly, this method was used as the key step in an asymmetric synthesis of letermovir.

Phosphoramidite

Sulfonyl

10.1002/anie.201709681

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Citations (77)

Asymmetric S‐Arylation of Sulfenamides to Access Axially Chiral Sulfilimines Enabled by Anionic Stereogenic‐at‐Cobalt(III) Complexes

Angewandte Chemie (2024)

Hua‐Jie Jiang Fang Wei Yan-Dong Meng Shu-Ying Ding J.J. Wang

Stereocenter

10.1002/ange.202419596

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Merging Visible-Light Photoredox and Chiral Phosphate Catalysis for Asymmetric Friedel–Crafts Reaction with in Situ Generation of N-Acyl Imines

Organic Letters (2019)

Meng‐Lan Shen Yang Shen Pu‐Sheng Wang

In the presence of visible-light photoredox and chiral phosphate catalysts, a novel asymmetric Friedel–Crafts reaction of indoles and readily accessible α-amino acid derived redox-active esters is established to afford enantioenriched 1-indolyl-1-alkylamine derivatives in moderate to high yields and with high levels of enantioselectivities. This method not only shows a mild and efficient alternative for the in situ generation of N-acyl imines but also indicates the feasibility of a multicatalyst system for asymmetric photoredox catalysis.

Photoredox catalysis

Friedel–Crafts reaction

Visible spectrum

10.1021/acs.orglett.9b00442

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Citations (52)

Light-Mediated Chiral Phosphate Catalysis for Asymmetric Dicarbofunctionalization of Enamides

ACS Catalysis (2020)

Yang Shen Meng‐Lan Shen Pu‐Sheng Wang

A light-mediated asymmetric dicarbofunctionalization of enamides with carboxylic-acid-derived redox-active esters (RAEs) and indoles has been established by using chiral lithium phosphate catalysis in the presence or absence of photoredox catalyst. This reaction features mild reaction conditions and broad substrate scopes, delivering a wide range of highly functionalized chiral amine derivatives. Mechanistic studies suggest that chiral lithium phosphate can serve as a pocket to accelerate the aggregation of enamide and RAE through hydrogen-bonding and coordination interaction, enabling the formation of a charge-transfer complex (CTC). Either enamide or CTC can be excited by direct irradiation or Ru(II)-mediated photosensitization to furnish chiral iminium intermediates for the asymmetric Friedel–Crafts reaction of indole.

Iminium

Photoredox catalysis

10.1021/acscatal.0c02660

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Citations (44)

Access to Chiral Hydropyrimidines through Palladium‐Catalyzed Asymmetric Allylic C−H Amination

Angewandte Chemie (2017)

Pu‐Sheng Wang Meng‐Lan Shen Tian‐Ci Wang Hua‐Chen Lin Liu‐Zhu Gong

Phosphoramidite

Sulfonyl

10.1002/ange.201709681

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Citations (18)