ChemInform Abstract: Intramolecular Alkylations of Aromatic Compounds. Part 29. Synthesis and Assignment of Absolute Configuration of 1-Acetylindoline-3-carboxylic Acid.

ChemInform ◽  
1990 ◽  
Vol 21 (42) ◽  
Author(s):  
E. REIMANN ◽  
T. HASSLER ◽  
H. LOTTER
Keyword(s):  
Carboxylic Acid ◽  
Absolute Configuration ◽  
Aromatic Compounds

A Simplified Protocol for the ortho-Deuteration of Acidic Aromatic Compounds in D2O

2019 ◽  
Author(s):  
Alyssa Garreau ◽  
Hanyang Zhou ◽  
Michael Young
Keyword(s):  
Carboxylic Acid ◽  
Aromatic Compounds ◽  
Large Scale ◽  
Simplified Approach ◽  
Directing Group ◽  
Large Scale Synthesis

<div>Methods to catalytically introduce deuterium in synthetically useful yields ortho to a carboxylic acid directing group on arenes typically requires D2 or CD3CO2D, which makes using these approaches cost prohibitive for large scale synthesis (equipment and reagent costs respectively). Herein we present a simplified approach using catalytic RhIII and D2O as deuterium source, and show its application to H/D exchange on various acidic substrates.</div>

A Simplified Protocol for the ortho-Deuteration of Acidic Aromatic Compounds in D2O

2019 ◽  
Author(s):  
Alyssa Garreau ◽  
Hanyang Zhou ◽  
Michael Young
Keyword(s):  
Carboxylic Acid ◽  
Aromatic Compounds ◽  
Large Scale ◽  
Simplified Approach ◽  
Directing Group ◽  
Large Scale Synthesis

<div>Methods to catalytically introduce deuterium in synthetically useful yields ortho to a carboxylic acid directing group on arenes typically requires D2 or CD3CO2D, which makes using these approaches cost prohibitive for large scale synthesis (equipment and reagent costs respectively). Herein we present a simplified approach using catalytic RhIII and D2O as deuterium source, and show its application to H/D exchange on various acidic substrates.</div>

Absolute configuration determination of theanti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization withL-prolinol

2013 ◽  
Vol 69 (11) ◽  
pp. 1411-1413 ◽  
Author(s):  
Yuko Kawanami ◽  
Hidekazu Tanaka ◽  
Jun-ichi Mizoguchi ◽  
Nobuko Kanehisa ◽  
Gaku Fukuhara ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Circular Dichroism ◽  
Carboxylic Acid ◽  
Absolute Configuration ◽  
Void Space ◽  
Circular Dichroism Spectra ◽  
The Absolute ◽  
Circular Dichroïsm ◽  
Hydrogen Bonded

The absolute configuration has been established of the enantiopureanti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with L-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl)pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO+·C30H19O4−·CH2Cl2. In the crystal structure, the AC dimer interacts with L-prolinol through a nine-membered hydrogen-bonded ring [R22(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoreticalversusexperimental circular dichroism spectra.

scholarly journals Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 6023
Author(s):  
Roberta Listro ◽  
Giacomo Rossino ◽  
Serena Della Volpe ◽  
Rita Stabile ◽  
Massimo Boiocchi ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Bioactive Compounds ◽  
Absolute Configuration ◽  
Chiral Center ◽  
Reference Compound ◽  
Enantiomeric Resolution ◽  
Enantiomerically Pure ◽  
X Ray ◽  
The Past ◽  
Configuration Assignment

During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams.

Direct halogenation of organic compounds with halides using oxone in water — A green protocol

2009 ◽  
Vol 87 (12) ◽  
pp. 1675-1681 ◽  
Author(s):  
H. Firouzabadi ◽  
N. Iranpoor ◽  
S. Kazemi
Keyword(s):  
Carboxylic Acid ◽  
Organic Compounds ◽  
Aromatic Compounds ◽  
Large Scale ◽  
Unsaturated Alcohol ◽  
Green Protocol ◽  
Unsaturated Carboxylic Acid

Direct bromination and iodination of various aromatic compounds with NaBr and NaI using oxone (2KHSO5·KHSO4·K2SO4) in water was accomplished successfully in high-to-excellent yields. The main benefit of this protocol is the performance of the reactions in water in the presence of a harmless oxidant without the use of any organic co-solvents. Using NaBr and NaI as the safe sources of halogens is another advantage of the protocol. This method is easily applicable to the large-scale operations. We have also applied this method successfully for the iodocyclization of an unsaturated alcohol and an unsaturated carboxylic acid.

The Resolution and Absolute Configuration of 2,3-Methanopyroglutamic Acid, 3-Oxo-2-azabicyclo[3,1,0]hexane-1-carboxylic Acid

1992 ◽  
Vol 65 (10) ◽  
pp. 2668-2671 ◽  
Author(s):  
Hiroaki Kodama ◽  
Shinichi Matsui ◽  
Michio Kondo ◽  
Charles H. Stammer
Keyword(s):  
Carboxylic Acid ◽  
Absolute Configuration
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