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Imidodiphosphorimidates (IDPis): Catalyst Motifs with Unprecedented Reactivity and Selectivity

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Chinese Journal of Chemistry 2023年第6期41卷 685-694页

作者： Jun Kee Cheng shao-hua xiang Bin Tan Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhenGuangdong 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhenGuangdong 518055China

The conceptually designed imidodiphosphorimidates(IDPis)have emerged as one of the most potent classes of chiral acid *** are characterized by enzyme-like,highly confined active site and high acidity,which underlie their wide-reaching applications as Bronsted acid catalysts and as precatalysts for silylium Lewis *** carbon-carbon and carbon-heteroatom bond formation reactions that were deemed intractable could now be attained with spectacular reactivity and *** that are small,unbiased and/or possess insufficient reactivity such as simple alkenes could now be *** high structural confinement is particularly invaluable to control stereo-and *** well-defined steric environment offers unique opportunity to control high-energy but structurally unbiased cation intermediates such as the norbonyl *** practical appeals such as good scalability as well as ease and modularity of preparation,the extremely low pre-catalyst loadings required to achieve high turnover and stereoselectivity have also come to define a new frontier in organocatalysis.

关键词： Bronsted acid catalyst Lewis acid catalyst Silylium ACDC Imidodiphosphorimidates Asymmetric organocatalysis

Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid

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Science China Chemistry 2020年第1期63卷 47-54页

作者： Jian Zhang Yi-Yan Wang He Sun shao-Yu Li shao-hua xiang Bin Tan School of Chemistry and Chemical Engineering Harbin Institute of TechnologyHarbin 150001China Department of Chemistry and Shenzhen Grubbs Institute Southern University of Science and TechnologyShenzhen 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhen 518055China

A catalytic enantioselective three-component Ugi reaction was ***-derived phosphoric acid with bulky 2,4,6-tricyclohexylphenyl groups at the 6,6′positions was found to be the best catalyst to affordα-amino amide derivatives in good to excellent yields(62%to 99%)and enantiocontrol(81%to>99%enantiomeric excess).This asymmetric reaction was applicable well to an array of aliphatic *** gram-scale synthesis,modification of dapsone,and enantioselective synthesis of(R)-Lacosamide underline the general utility of this *** of dihedral angles and substituents of the chiral phosphoric acids on the enantioselectivity was also discussed in this article.

关键词： α-amino amide Ugi reaction chiral phosphoric acid enantioselectivity Lacosamide

Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Axially Chiral Compounds

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Chinese Journal of Chemistry 2021年第7期39卷 1787-1796页

作者： Bing-Chao Da shao-hua xiang shaoyu Li Bin Tan Department of Chemistry and Shenzhen Grubbs Institute Southern University of Science and TechnologyShenzhenGuangdong 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhenGuangdong 518055China

The well-defined conformational properties of axially chiral compounds bring extraordinary values to an assortment of bioactive molecules,advanced materials,organocatalysts as well as chiral ligands in asymmetric *** demonstrated usefulness and untapped potential of axially chiral structural motifs stimulate increasing efforts to develop novel and efficient approaches for their *** this regard,the chiral phosphoric acids broadly used in asymmetric Brønsted acid catalysis have shown high relevance for atroposelective synthesis as *** strong interest in reaction chemistry of atropisomers has established a rewarding research programme in our *** course of studies will be recounted in this account,with discussion focused on the use of chiral phosphoric acids to catalyze construction of several key axially chiral structures such as BINAM,BINOL,NOBIN,arylquinones,SPINOL,arylpyrrole analogues and axially chiral alkenes.

关键词： Axial chirality Organocatalysis Chiral phosphoric acid Biaryls Asymmetric synthesis

Alternative non-Gaussianity measures for quantum states based on quantum fidelity

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Chinese Physics B 2022年第3期31卷 192-200页

作者： Cheng xiang Shan-Shan Li Sha-Sha Wen shao-hua xiang College of Electrical and Information Engineering Huaihua UniversityHuaihua 418008 China Hunan Provincial Key Laboratory of Ecological Agriculture Intelligent Control Technology Huaihua 418008China

We propose three alternative measures for non-Gaussianity of quantum states: sine distance, Bures angle, and Bures distance, which are based on quantum fidelity introduced by Wang [Phys. Lett. A 373 58(2008)]. Using them, we evaluate the non-Gaussianity of some relevant single-mode and two-mode non-Gaussian states and find a good consistency of the three examined measures. In addition, we show that such metrics can exactly quantify the degree of Gaussianity of even Schrödinger-cat-like states of small amplitudes that can not be measured by other known non-Gaussianity measures such as the Hilbert–Schmidt metric and the relative entropy metric. We make a comparative study between all existing nonGaussianity measures according to the metric axioms and point out that the sine distance is the best candidate among them.

关键词： non-Gaussianity quantum fidelity non-Gaussian states sine metric

Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones

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Science China Chemistry 2021年第9期64卷 1515-1521页

作者： Ji-Wei Zhang Fei Jiang Ye-Hui Chen shao-hua xiang Bin Tan School of Chemistry and Chemical Engineering Harbin Institute of TechnologyHarbin150001China Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and TechnologyShenzhen518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhen518055China

Privileged biaryl frameworks,BINOL and NOBIN,were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction *** judicious selection of palladium-catalytic system plays a pivotal role in the excellent *** transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthylamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high ***,the bromosubstituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of conditions,providing an effective handle for further enriching the library of BINOLs and *** attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis.

关键词： BINOLs NOBINs high selectivity C-H arylation palladium-catalysis

Direct Construction of NOBINs via Domino Arylation and Sigmatropic Rearrangement Reactions

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Chinese Journal of Chemistry 2020年第12期38卷 1503-1514页

作者： Ji-Wei Zhang Liang-Wen Qi shaoyu Li shao-hua xiang Bin Tan School of Chemistry and Chemical Engineering Harbin Institute of TechnologyHarbinHeilongjiang 150001China Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and TechnologyShenzhenGuangdong 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhenGuangdong 518055China

of main observation and conclusion Privileged 2-amino-2,-hydroxy-l/l,-binaphthyl(NOBIN)frameworks were constructed through a novel domino arylation of naphthylhydroxylamines with diarylhalonium salts and sigmatropic rearrangement in a transition metal-free *** protocol bears broad substrate generality and proceeds under mild reaction conditions,affording diversified NOBINs in high efficiency with absolute regiocontrol during the rearrangement *** active product was accessible by chiral A/-heterocyclic carbene-catalyzed kinetic resolution in one pot or diastereoselective[3,3]-rearrangement guided by a removable chiral ***,diarylchloronium and diarylbrominium salts have been employed as arylation reagents for the first time in assembling such representative biaryl frameworks.

关键词： process. rearrangement salts

Skeletal Editing of Cyclic Molecules Using Nitrenes

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Chinese Journal of Chemistry 2024年第21期42卷 2656-2667页

作者： Yi-An Xu shao-hua xiang Jin-Teng Che Yong-Bin Wang Bin Tan Shenzhen Grubbs Institute Department of ChemistrySouthern University of Science and TechnologyShenzhenGuangdong518055 China

Nitrenes,as neutral monovalent nitrogen-centered molecular species,can insert into various bond or remove nitrogen atoms from *** assisted single-atom skeletal editing,discovered decades ago,provides an efficient approach for the precise alteration of cyclic *** this review,we briefly summarize early studies on skeletal editing of cyclic frameworks involving nitrene species,and introduce several recent important advances systematically.

关键词： Nitrenes Skeletal Editing Cyclic Compounds Atom exchange Late-stage modification

Atroposelective Synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles

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Chinese Journal of Chemistry 2024年第7期42卷 731-735页

作者： Wen Bao Ye-Hui Chen Yu-Wei Liu shao-hua xiang Bin Tan School of Pharmacy&StateKey Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhouGansu 730000China Shenzhen Grubbs Institute Department of ChemistrySouthern University of Science and TechnologyShenzhenGuangdong 518055China

Indole-based atropisomers are a very important class of axially chiral ***,the atroposelective synthesis of axially chiral 2-arylindole remains largely *** this study,we report the successful synthesis of atropisomeric 2-arylindoles using direct amination of indoles with p-quinonediimines in the presence of chiral phosphoric acid as a *** acts as an aminating reagent through formal polarity inversion of *** malonate group on the 2-aryl of 2-indoles was found to be essen-tial for high enantioselectivity of the *** could be due to the additional interaction between the ester group and the cata-lyst,as well as the intramolecular hydrogen *** findings provide a new strategy for the asymmetric construction of 2-arylindole atropisomers.

关键词： Chiral phosphoric acid Quinonediimines Direct amination Nucleophilic addition Asymmetric catalysis Enantioselectivity Axially chiral 2-arylindole Atroposelective synthesis

Stereoselective Construction of Complex Spirooxindoles via Bisthiourea Catalyzed Three-Component Reactions

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Chinese Journal of Chemistry 2018年第12期36卷 1182-1186页

作者： Lin-Lin Zhang Ji-Wei Zhang shao-hua xiang Zhen Guo Bin Tan College of Material Science & Engineering Taiyuan University of Technol- ogyTaiyuanShanxi 030024China Department of Chemistry South University of Science and Technology of ChinaShenzhenGuangdong 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhenGuangdong 518055China

A well‐designed three‐component reaction was developed to construct a class of optically active carbazolespirooxindole‐urazoles in good yields with excellent stereoselectivities via tandem Diels‐Alder reaction and ene‐reaction. The driving force originating from aromatization with in situ generated carbazolespirooxindole and the high reactivity of 4‐phenyl‐3H‐1,2,4‐triazole‐3,5‐dione facilitate the ene‐reaction in mild conditions. Control experiments indicated that the excellent stereoselectivities of ene‐reaction most likely came from the spatial configuration of the carbazolespirooxindole. The obtained products could be converted to other synthetic useful structures via diverse functionalization.

关键词： multicomponent reactions asymmetric catalysis bisthiourea Diels‐Alder reaction ene‐reaction complex spirooxindoles