Zhichao Jin’s research while affiliated with Guizhou University and other places

... Concurrently, our group has developed a versatile approach to synthesizing planar chiral [2.2]paracyclophanes over NHCs 24 . Despite these advances 25 , to the best of our knowledge, NHC-mediated desymmetrisation has never been used to prepare inherently chiral products 26 . ...

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Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes

... So far, catalytic asymmetric catalysis has proven to be a versatile tool for the enantioselective synthesis of different chiral agrochemicals 32 and novel drugs in medicinal chemistry. 33 Therefore, the use of chiral catalysts to transfer and enhance chirality in chemical reactions is also a priority in manufacturing of current active chiral ingredients. ...

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The continuing significance of chiral agrochemicals

... Plant diseases cause huge losses in the world's crops every year, resulting in reduced crop yields and threatening food safety. 1 Different types of fungicides have been widely used in agriculture to solve these problems. 2,3 However, the long-term use of current commercial fungicides has resulted in increasing resistance of plant pathogenic fungi, which not only makes plant disease control less efficient but also increases the cost of pesticide usage and the threat of pesticide residue to the environment. 4 Therefore, it is particularly important to develop new chemical fungicides that are efficient, environmentally friendly, and broad-spectrum to overcome the developed resistance. ...

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Synthesis, antifungal activity, and molecular simulation study of nootkatone‐based thiazole‐hydrazone compounds as novel succinate dehydrogenase inhibitor

... Herbicidal activity tests and data evaluation were performed at application rates of 75 to 150 g ai/ha, referencing methods reported in previous literature. 36,37 Weed seeds were planted in plastic pots with an inner diameter of 8 cm and incubated in a greenhouse under alternating temperatures of 15°C (night, 12 h) and 25°C (day, 12 h). After approximately 2 weeks, both Abutilon theophrasti and Digitaria sanguinalis reached the third leaf stage. ...

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Discovery of novel benzoxazinone derivatives as promising protoporphyrinogen IX oxidase inhibitors

... 27 Recent sequential work by Li et al.'s group 28 has developed a series of potential fungicidal candidate containing chiral oxazoline ( Fig. 1(B)) as SDHIs and found that fine-tuning the chiral substituent of the oxazoline significantly affects the antifungal activities. In addition, indole derivatives containing different chiral oxazoline moieties ( Fig. 1(C)) designed by Huang et al. 29 exhibited significantly different biological activities against Potato virus Y (PVY). Encouraged by these works, we envisage that this interesting chiral oxazoline scaffold could facilitate the development of novel pesticides. ...

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Design and development of pyrazol‐5‐ylbenzamide derivatives containing chiral oxazoline moiety as fungicides based on molecular docking

... Li and co-workers [85] described the first carbene-catalyzed regio-and enantioselective C-7 alkylated indoles. The reaction between 4-aminoindoles 204 and α-bromoenals 205 is furnished C-7 alkylated indoles substrates 206 in moderate to good yields with good to excellent enantioselectivities (Scheme 68). ...

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Strategies Employing Transition‐Metal Free Conditions for C−C Bond Formation in Indoles

... Inspired by Collins' dual-catalysis model 47 and Wang's desymmetrization approach for the synthesis of medium-sized ring 48 , it was envisioned that the desymmetrization of 1,3-diols by an intramolecular N-heterocyclic carbene (NHC)-bound acyl azolium would achieve macrocyclization and stereoselective control over the two chiral elements [49][50][51][52][53] . Furthermore, although the hydrogen bonding of a chiral phosphoric acid (CPA) catalyst with 1,3-diols offers enhanced diastereoselectivities ( Fig. 1E) 48 , this approach is challenging due to several difficulties. ...

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Enantio-, atrop-, and diastereoselective macrolactonization to access type III cyclophanes

... Ni-catalyzed and photoredox processes (Scheme 21). [49] Under blue LEDs irradiation with 4-CzIPN, glycosyl bromides and redox-active dihydropyridines derived from amino acids and peptides reacted to afford the C-glycosyl amino acids or C-glycosyl peptides with excellent α-stereoselectivities when employing metalcatalyst Ni(acac) 2 and ligand (S,S)-2,2-bis(4phenyl-2-oxazolin-2-yl)propane ((S,S)-Ph-Box). All 20 natural amino acids, peptides, and their derivatives could undergo this C-glycosylation. ...

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Recent Advances in Organic Photocatalyst‐Promoted Carbohydrate Synthesis and Modification under Light Irradiation

... Recently, Wu, Jin et al. reported an atroposelective DKR acylation reaction for the enantioselective preparation of axially chiral biaryls with an aldehyde fragment. [31] Racemic biaryl aldehydes 39 bearing intrinsic axes and α-bromoenals 40 were used as the starting materials, together with employing NHC Cat. 11* as the key organocatalyst. ...

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Research Progress on Organocatalytic Asymmetric Synthesis of Atropisomeric Aldehydes

... Recently, Chi et al. developed a modular 2-fold "taggingediting" strategy for synthesizing the C3-or C6-selective, and C6-/C3-selective (double) deoxygenated saccharides (Scheme 73). [116] In the presence of NHC precatalyst (A1)/boronic acid (A2), unprotected glucosides were selectively acylated to the C3À OH-acylated sugar using photoredox ester (A3) as an acylation reagent. The acylation saccharides underwent photopromoted CÀ O bond cleavage with 4-CzIPN to afford the deoxygenated sugars. ...

Reference:

Recent Advances in Organic Photocatalyst‐Promoted Carbohydrate Synthesis and Modification under Light Irradiation