scholarly journals Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxazolines

2021 ◽  
Author(s):  
Ayham Abazid ◽  
Tom-Niklas Hollwedel ◽  
Boris Nachtsheim
Keyword(s):  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Iodine Compound

This manuscript describes a highly enantioselective oxidative cyclization of N-Allyl Benzamides and derivatives thereof. This method uses a chiral triazole-based iodine catalyst to generate a hypervalent iodine compound in situ as the active catalytic species. Besides oxazolines, other N-heterocylces such as thiazolines, imidazolines as well as oxanines can be generated in high optical purities. <br>

scholarly journals Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxazolines

2021 ◽  
Author(s):  
Ayham Abazid ◽  
Tom-Niklas Hollwedel ◽  
Boris Nachtsheim
Keyword(s):  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Iodine Compound

This manuscript describes a highly enantioselective oxidative cyclization of N-Allyl Benzamides and derivatives thereof. This method uses a chiral triazole-based iodine catalyst to generate a hypervalent iodine compound in situ as the active catalytic species. Besides oxazolines, other N-heterocylces such as thiazolines, imidazolines as well as oxanines can be generated in high optical purities. <br>

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2907-2912 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Satoshi Minakata ◽  
Kenta Takemoto ◽  
Shunsuke Yahata ◽  
Takumi Kojima
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acids ◽  
Present Method ◽  
Medicinal Chemistry ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
Unsaturated Carboxylic Acids

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5H)-ones or furan-2(3H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

Direct oxidative cyanation of tertiary amines promoted by in situ generated hypervalent iodine(III)-CN intermediate

2015 ◽  
Vol 56 (41) ◽  
pp. 5628-5631 ◽  
Author(s):  
Hang Shen ◽  
Xiaohui Zhang ◽  
Qing Liu ◽  
Jing Pan ◽  
Wen Hu ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
Tertiary Amines

Convenient Synthesis of Oxazolo[5,4-h]pyrrolo[4,3,2-de]quino­lones via Hypervalent Iodine Mediated Intramolecular Oxidative Cyclization

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4517-4522
Author(s):  
Li-Ping Sun ◽  
Chun-Meng Wang ◽  
Sheng-Wei Yang ◽  
Kai-Xiang Tang ◽  
Tian-Hong Gao ◽  
...  
Keyword(s):  
Functional Groups ◽  
Practical Method ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Air Atmosphere ◽  
Convenient Synthesis ◽  
Reaction Proceeds ◽  
Intramolecular Oxidative Cyclization

A convenient and practical method has been developed for the synthesis of substituted oxazolo[5,4-h]pyrrolo[4,3,2-de]quinolones via the intramolecular oxidative cyclization by using PIFA as oxidant and TMSOTf as additive in DCE under an air atmosphere. The reaction proceeds in good yields and has good functional groups tolerance.

Preparation of an aliphatic-substituted hypervalent iodine compound, tetracoordinate 1,2-iodoxetane 1-oxide, and its application to oxidation

2004 ◽  
Vol 45 (44) ◽  
pp. 8173-8175 ◽  
Author(s):  
Naokazu Kano ◽  
Masaki Ohashi ◽  
Kazuhisa Hoshiba ◽  
Takayuki Kawashima
Keyword(s):  
Hypervalent Iodine ◽  
Iodine Compound

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.

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