Hypervalent Iodine(III)-Mediated Oxidative Decarboxylation of β,γ-Unsaturated Carboxylic Acids

2014 ◽  
Vol 16 (17) ◽  
pp. 4646-4649 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Shunsuke Yahata ◽  
Takumi Kojima ◽  
Satoshi Minakata
Keyword(s):  
Carboxylic Acids ◽  
Hypervalent Iodine ◽  
Oxidative Decarboxylation ◽  
Unsaturated Carboxylic Acids

ChemInform Abstract: Hypervalent Iodine(III)-Mediated Oxidative Decarboxylation of β,γ-Unsaturated Carboxylic Acids.

ChemInform ◽  
2015 ◽  
Vol 46 (9) ◽  
pp. no-no
Author(s):  
Kensuke Kiyokawa ◽  
Shunsuke Yahata ◽  
Takumi Kojima ◽  
Satoshi Minakata
Keyword(s):  
Carboxylic Acids ◽  
Hypervalent Iodine ◽  
Oxidative Decarboxylation ◽  
Unsaturated Carboxylic Acids

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.

ChemInform Abstract: Reaction of β,γ-Unsaturated Carboxylic Acids with Thallium Triacetate (TTA): Lactonization vs Oxidative Decarboxylation.

ChemInform ◽  
2010 ◽  
Vol 30 (32) ◽  
pp. no-no
Author(s):  
Helena M. C. Ferraz ◽  
Monica V. A. Grazini ◽  
Luiz F. Silva Jr. ◽  
Luiz S. Longo Jr.
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Decarboxylation ◽  
Unsaturated Carboxylic Acids

Perturbation theory of substituent effect. Importance of the field effect in transmission of the substituent effect

1980 ◽  
Vol 45 (6) ◽  
pp. 1655-1661 ◽  
Author(s):  
Robert Ponec
Keyword(s):  
Perturbation Theory ◽  
Carboxylic Acids ◽  
Quantum Chemical ◽  
Substituent Effect ◽  
Field Effect ◽  
Adequate Description ◽  
Meta Position ◽  
Unsaturated Carboxylic Acids

Various quantum chemical approaches to the problem of transmission of the substituent effect were compared. It was shown that inclusion of the electronic repulsion (field effect) was necessary to give a true picture of differences in ρ constants for reactions of the cis and trans isomers of substituted unsaturated carboxylic acids; the same holds for an adequate description of transmission of the substituent effect from the meta position on a given skeleton.

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

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