Martin's Sulfurane DOI

Brian A. Roden,

Kyriaki Gennaiou,

Maria Kourgiantaki

et al.

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 10

Published: July 17, 2024

Abstract image [ 32133‐82‐7 ] C 30 H 20 F 12 O 2 S (MW 672.57) InChI = 1S/C30H20F12O2S/c31‐27(32,33)25(28(34,35)36,21‐13‐5‐1‐6‐14‐21)43‐45(23‐17‐9‐3‐10‐18‐23,24‐19‐11‐4‐12‐20‐24)44‐26(29(37,38)39,30(40,41)42)22‐15‐7‐2‐8‐16‐22/h1‐20H InChIKey RMIBJVUYNZSLSD‐UHFFFAOYSA‐N (dehydration of alcohols; synthesis epoxides and cyclic ethers; 3 cleavage amides; 5 oxidation amines 6 ) Physical Data : mp 107–109 °C. Solubility sol ether, benzene, acetone, alcohols. Form Supplied in white crystals. Analysis Reagent Purity NMR, IR. Preparative Method by the reaction potassium salt 1,1,1,3,3,3‐hexafluoro‐2‐phenylisopropanol with diphenyl sulfide presence chlorine ether at −78 1 a Handling, Storage, Precautions avoid moisture; readily hydrolyzed; stable rt; decomposes slowly rt solution.

Language: Английский

Organocatalytic enantioselective construction of Si-stereocenters: recent advances and perspectives DOI

Zhong-Tian Ye,

Zhongwei Wu,

Xue‐Xin Zhang

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(17), P. 8546 - 8562

Published: Jan. 1, 2024

Silicon-stereogenic chiral organosilanes have found increasing applications in synthetic chemistry, medicinal and materials science. In this context, various asymmetric catalytic methods been established for the diverse synthesis of silicon-stereogenic silanes. particular, organocatalysis is emerging as an important complementary tool enantioselective construction silicon-stereocenters, along with rapid development chiral-metal catalyzed protocols. Its advent provides a powerful platform to achieve functionalized structural diversity, should lead great organosilicon chemistry. Tutorial Review, we highlight these latest achievements from two aspects: desymmetrizations prochiral tetraorganosilanes dynamic kinetic transformations racemic by employing five organocatalytic activation modes. The advantages, limitations value each protocol, well opportunities still open further exploration, are also discussed.

Language: Английский

Citations

13
Modular Assembly of Six‐Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade DOI
Feng‐Cheng Jia,

Zi‐Yi Yuan,

Na Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2614 - 2620

Published: July 3, 2024

Comprehensive Summary Concise assembly of spirooxindoles is great significance but a challenging task in modern organic synthesis. Described herein an unusual base‐promoted [4+2] spiroannulation rarely used isatin‐derived β‐silylcarbinols with o ‐halogen aromatic ketones, which enables rapid and modular synthesis six‐membered carbocyclic high yields excellent functional group tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved Peterson olefination, Michael addition intramolecular C(sp 3 ) arylation cascade. The variegated synthetic derivatization target products successful construction bioactive molecules further illustrate the potential spirooxindole‐related drug discovery.

Language: Английский

Citations

4
Construction of axial and point chirality through Ni-catalyzed sila-cycloaddition reaction via desymmetrization and (dynamic) kinetic resolution DOI
Hua‐Jie Zhu, Minghao Shen,

Jia-Wei Si

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

Language: Английский

Citations

0
Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds DOI Open Access

Yan Zeng,

Fei Ye

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(10), P. 3388 - 3388

Published: Jan. 1, 2023

In the past two decades, organosilicon compounds bearing silicon-stereogenic centers have attracted extensive attention in fields of organic synthesis, materials, and drug design.However, expansion these has been greatly restricted by limited source compounds.Therefore, development highly efficient selective asymmetric catalytic methods to obtain chiral with is a challenging task that needs be solved urgently.The latest research progress on new reaction systems for synthesis center containing organosilanes since 2011 mainly summarized.

Language: Английский

Citations

7
Chromium(III)-Catalyzed Desymmetrization of meso-Epoxides via Remote Stereocontrol: Synthesis of Chiral Fluorenes Bearing All-Carbon Quaternary Stereocenters DOI
Ying Zhou,

Feng Jiang,

Xin Yue

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 877 - 882

Published: Jan. 24, 2024

An asymmetric desymmetrization of fluorene-derived meso-epoxides is disclosed for the construction chiral fluorenes bearing an all-carbon quaternary stereocenter at C9. This catalyzed by a (salen)CrIII complex via remote stereocontrol, producing diverse with excellent yields and stereoselectivity. The practicality this protocol was demonstrated through transformation obtained products to some intriguing enantioenriched polymerizable monomers.

Language: Английский

Citations

2
Pd-catalyzed intermolecular Si–O formation via Si–C activation DOI
Shuang Liu, Yushu Chen, Yichen Wu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(8), P. 2661 - 2669

Published: June 26, 2024

Language: Английский

Citations

2
Catalytic Asymmetric Synthesis of Chiral Fluorenes: Recent Developments and Future Perspectives DOI

Tianyuan Ou,

Liming Xiang,

Ying Zhou

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 26, 2024

Abstract The chiral fluorene fragment constitutes one of the most important scaffolds frequently found in numerous bioactive molecules, ligands, and advanced functional materials due to its unique physical properties. In this context, various transition metal‐ organo‐catalyzed asymmetric reactions have been developed prepare fluorenes with high optical purity. present mini‐review, we summarize fifteen years achievements catalytic synthesis their derivatives. Particular attention is given strategies used mechanistic aspects some significant reactions. Moreover, cutting‐edge developments silafluorenes are also highlighted.

Language: Английский

Citations

0
Silver‐Catalyzed Olefination of Aryl Aldehydes Using Propiolates DOI

Rina Raju Manwar,

Rengarajan Balamurugan

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(48)

Published: June 11, 2024

Olefination of aldehydes is one the fundamental reactions in organic synthesis. The commonly used Wittig olefination reaction however uses stoichiometric quantities reagents under basic conditions resulting amounts byproducts. Known catalytic alternate to requires silane reducing agents and high temperature. Herein, we report a base-free aryl using propiolates as surrogate for Witting reagent silver catalysis. Trimethyl orthoformate, presence catalyst adds alkynoate form nucleophilic allenolate which reacts with reactive oxocarbenium ion formed from aldehyde conditions. Subsequently, decarbonylation occurs olefin. Trans olefin exclusively simple cinnamaldehydes. Such conceptually novel has not been explored so far.

Language: Английский

Citations

0
Martin's Sulfurane DOI

Brian A. Roden,

Kyriaki Gennaiou,

Maria Kourgiantaki

et al.

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 10

Published: July 17, 2024

Abstract image [ 32133‐82‐7 ] C 30 H 20 F 12 O 2 S (MW 672.57) InChI = 1S/C30H20F12O2S/c31‐27(32,33)25(28(34,35)36,21‐13‐5‐1‐6‐14‐21)43‐45(23‐17‐9‐3‐10‐18‐23,24‐19‐11‐4‐12‐20‐24)44‐26(29(37,38)39,30(40,41)42)22‐15‐7‐2‐8‐16‐22/h1‐20H InChIKey RMIBJVUYNZSLSD‐UHFFFAOYSA‐N (dehydration of alcohols; synthesis epoxides and cyclic ethers; 3 cleavage amides; 5 oxidation amines 6 ) Physical Data : mp 107–109 °C. Solubility sol ether, benzene, acetone, alcohols. Form Supplied in white crystals. Analysis Reagent Purity NMR, IR. Preparative Method by the reaction potassium salt 1,1,1,3,3,3‐hexafluoro‐2‐phenylisopropanol with diphenyl sulfide presence chlorine ether at −78 1 a Handling, Storage, Precautions avoid moisture; readily hydrolyzed; stable rt; decomposes slowly rt solution.

Language: Английский

Citations

0