scholarly journals A survey of chiral hypervalent iodine reagents in asymmetric synthesis

2018 ◽  
Vol 14 ◽  
pp. 1244-1262 ◽  
Author(s):  
Soumen Ghosh ◽  
Suman Pradhan ◽  
Indranil Chatterjee
Keyword(s):  
Transition Metals ◽  
Asymmetric Synthesis ◽  
Environmentally Friendly ◽  
Hypervalent Iodine ◽  
Asymmetric Transformations ◽  
Iodine Chemistry

The recent years have witnessed a remarkable growth in the area of chiral hypervalent iodine chemistry. These environmentally friendly, mild and economic reagents have been used in catalytic or stoichiometric amounts as an alternative to transition metals for delivering enantioenriched molecules. Varieties of different chiral reagents and their use for demanding asymmetric transformations have been documented over the last 25 years. This review highlights the contribution of different chiral hypervalent iodine reagents in diverse asymmetric conversions.

The aryl iodine-catalyzed organic transformation via hypervalent iodine species generated in situ

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Xuemin Li ◽  
Guangchen Li ◽  
Yifu Cheng ◽  
Yunfei Du
Keyword(s):  
Organic Synthesis ◽  
Oxidative Coupling ◽  
Hypervalent Iodine ◽  
Organic Transformations ◽  
Aryl Iodide ◽  
Oxidative Reaction ◽  
Iodine Species ◽  
Iodine Chemistry

Abstract The application of hypervalent iodine species generated in situ in organic transformations has emerged as a useful and powerful tool in organic synthesis, allowing for the construction of a series of bond formats via oxidative coupling. Among these transformations, the catalytic aryl iodide can be oxidized to hypervalent iodine species, which then undergoes oxidative reaction with the substrates and the aryl iodine regenerated again once the first cyclic cycle of the reaction is completed. This review aims to systematically summarize and discuss the main progress in the application of in situ-generated hypervalent iodine species, providing references and highlights for synthetic chemists who might be interested in this field of hypervalent iodine chemistry.

Introduction of Hypervalent Iodine Chemistry and Its Application

Daxue Huaxue ◽  
2019 ◽  
Vol 34 (2) ◽  
pp. 1-16
Author(s):  
Dan LIU ◽  
◽  
Jiahao HE ◽  
Chi ZHANG
Keyword(s):  
Hypervalent Iodine ◽  
Iodine Chemistry

Hypervalent iodine chemistry—recent advances and applications

Tetrahedron ◽  
2010 ◽  
Vol 66 (31) ◽  
pp. 5737-5738 ◽  
Author(s):  
Stéphane Quideau ◽  
Thomas Wirth
Keyword(s):  
Hypervalent Iodine ◽  
Recent Advances ◽  
Iodine Chemistry

Hypervalent iodine reactions utilized in carbon–carbon bond formations

2019 ◽  
Vol 17 (34) ◽  
pp. 7822-7848 ◽  
Author(s):  
I. F. Dempsey Hyatt ◽  
Loma Dave ◽  
Navindra David ◽  
Kirandeep Kaur ◽  
Marly Medard ◽  
...  
Keyword(s):  
Electrophilic Substitution ◽  
Hypervalent Iodine ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Recent Developments ◽  
Iodine Chemistry

This review covers recent developments of hypervalent iodine chemistry in dearomatizations, radicals, hypervalent iodine-guided electrophilic substitution, arylations, photoredox, and more.

scholarly journals Asymmetric synthesis: From transition metals to organocatalysis

2008 ◽  
Vol 80 (5) ◽  
pp. 953-966 ◽  
Author(s):  
Pavel Kočovský ◽  
Andrei V. Malkov
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Asymmetric Synthesis ◽  
Absolute Configuration ◽  
Nucleoside Analogs ◽  
Oxide Catalysts ◽  
Lewis Base ◽  
New Approach ◽  
Π Interactions ◽  
Metal Catalyzed

Umpolung in the allylation reaction is discussed with examples drawn from transition-metal-catalyzed allylic substitution (with the allylic unit acting as an electrophile) and Lewis base-catalyzed allylation of aldehydes with allyltrichlorosilane (with the allyl acting as a nucleophile). Iridium-catalyzed electrophilic allylation of O-nucleophiles has been employed in our new approach to C-nucleoside analogs, where the C-O bond (rather than C-C) was constructed stereospecifically. Variation of the absolute configuration in the starting segments allowed the synthesis of all four combinations of D/L-α/β-ribosides. In the nucleophilic allylation of aldehydes, chiral pyridine-type N-oxide catalysts are presented, in particular QUINOX and METHOX, and the intriguing behavior of QUINOX is discussed. Here, the π-π interactions between the substrate aldehyde and the catalyst are suggested to rationalize the experimental observations. Good correlation between the calculated energies for the transition states and the experimentally observed enantioselectivities has been obtained.

A FACILE PREPARATION OF 3-HALOFLAVONES USING HYPERVALENT IODINE* CHEMISTRY

2001 ◽  
Vol 31 (14) ◽  
pp. 2101-2106 ◽  
Author(s):  
Ho Sik Rho ◽  
Byoung-Seob Ko ◽  
Young-Sung Ju
Keyword(s):  
Hypervalent Iodine ◽  
Facile Preparation ◽  
Iodine Chemistry

scholarly journals Asymmetric Michael addition using sugar derived organocatalysts

2017 ◽  
Vol 17 (4) ◽  
pp. 182-196
Author(s):  
P.B. Lalthanpuii ◽  
C. Lalhriatpuia ◽  
K. Vanlaldinpuia
Keyword(s):  
Molecular Weight ◽  
Asymmetric Synthesis ◽  
Present Article ◽  
Asymmetric Catalysis ◽  
Michael Addition ◽  
Metal Contamination ◽  
Low Molecular Weight ◽  
Asymmetric Transformations ◽  
Asymmetric Michael Addition ◽  
Different Types

Sugars are low-molecular-weight carbohydrates which consist of polyhydroxyl and carbonyl (aldehyde or ketone) functional groups. Different types of compounds derived from sugars have been used extensively as powerful and effective catalysts for asymmetric synthesis. They are readily available at a reasonable price, easily prepared, no metal contamination and are inert towards moisture and air. They are highly functionalized and have well defined stereogenic centres. Most of them are employed as chiral ligands in metal based asymmetric catalysis and are used for various asymmetric transformations. Different compounds derived from sugars have also been used recently as organocatalysts for asymmetric synthesis. The present article provides some of the organocatalysts used for asymmetric synthesis.

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