53624-84-3Relevant academic research and scientific papers
BORON-BASED CYCLOADDITION CATALYSTS AND METHODS FOR THE PRODUCTION OF BIO-BASED TEREPHTHALIC ACID, ISOPHTHALIC ACID AND POLY (ETHYLENE TEREPHTHALATE)
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Paragraph 00171; 00187, (2017/04/11)
Methods for producing cycloaddition products comprising: reacting a diene with a dienophile in the presence of one or more boron-based catalysts of Formula I or Formula II are provided. In particular, the methods can be used to prepare 4-methyl-3-cyclohexene- 1-carboxylic acid and 3-methyl-3-cyclohexene-l-carboxylic acid, including bio-based versions thereof. The cycloaddition products can be advantageously used in the production of terephthalic acid and isophthalic acid, and ultimately, poly(ethylene terephthalate), and bio-based versions thereof. Formula I Formula II
Anti-MRSA agent discovery using diversity-oriented synthesis
Thomas, Gemma L.,Spandl, Richard J.,Glansdorp, Freija G.,Welch, Martin,Bender, Andreas,Cockfield, Joshua,Lindsay, Jodi A.,Bryant, Clare,Brown, Derek F. J.,Loiseleur, Olivier,Rudyk, Helene,Ladlow, Mark,Spring, David R.
supporting information; experimental part, p. 2808 - 2812 (2009/02/06)
Beating the superbugs: Diversity-oriented synthesis using a solid-supported phosphonate unit to synthesize 242 drug-like compounds based on 18 natural-productlike scaffolds led to the discovery of gemmacin (see scheme). This new structural class of antibiotic is active towards methicillin-resistant Staphylococcus aureus (MRSA). (Chemical Equation Presented).
SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,Kruchinin, Dennis,Key, Min-Suk,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Thomson, James E.
, p. 2945 - 2964 (2008/02/09)
The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.
Hydrophobic effects are dominant over secondary orbital interactions for a simple Diets-Alder reaction in salt solutions
Sarma, Diganta,Kumar, Anil
, p. 2199 - 2202 (2007/10/03)
The stereoselectivity ratios for a Diels-Alder reaction between cyclopentadiene with methyl trans-crotonate carried out in salt solutions demonstrate the dominance of hydrophobic effects over secondary orbital interactions.
Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels-Alder reactions
Lait, Susan M.,Parvez, Masood,Keay, Brian A.
, p. 749 - 756 (2007/10/03)
A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-1-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Die
DMAP-promoted racemization-free deacylation of carboxthioimide adducts: Carboxthioimide as a versatile carboxy protecting group
Su, Dah-Wei,Wang, Ying-Chuan,Yan, Tu-Hsin
, p. 545 - 546 (2007/10/03)
The DMAP-promoted deacylation of carboxthioimide adducts can be directed to form either acid or various ester protecting groups with no detectable levels of epimerization.
Zirconocene-catalyzed cationic Diels-Alder reactions
Wipf, Peter,Xu, Wenjing
, p. 4551 - 4562 (2007/10/02)
In situ prepared Cp2ZrCl+ catalyzes the formation of dioxolenium ions from α,β-unsaturated epoxy esters. As a consequence of this activation process, acrylate, methacrylate and crotonate derivatives undergo a rapid and stereoselective cationic [4+2] cycloaddition with a wide range of dienes. Ring-extended carboxylic acid derivatives are formed in 1-7 h at 0-21°C and in 50-90% yield after saponification of the intermediate diol esters. Simple Lewis acid catalysis by Cp2ZrCl+ can be excluded on the basis of the experimental results.
A stereoselective biocatalytic Diels-Alder reaction
Rao,Srinivasan,Bhanumathi
, p. 5959 - 5960 (2007/10/02)
Baker's yeast catalyzes the stereoselective Diels-Alder reaction of cyclopentadiene 1 with dienophiles 2, 4 and 6. A predominant formation of exo isomer is observed in some cases.
Asymmetric Diels-Alder Reaction Using (S)-Pyroglutamic Acid Derivatives as Chiral Dienophiles
Ikota, Nobuo
, p. 2219 - 2221 (2007/10/02)
Asymmetric Diels-Alder reaction of cyclopentadiene with chiral dienophiles (3) derived from (S)-pyroglutamic acid derivatives was performed in the presence of a Lewis acid such as diethylaluminium chloride in toluene to afford the cycloadducts with high diastereoselectivity.Keywords asymmetric reaction; Diels-Alder reaction; (S)-pyroglutamic acid; chiral dienophile; diethylaluminium chloride; (2+4)cycloaddition
Acyloxyborane: An Activating Device for Carboxylic Acids
Furuta, Kyoji,Miwa, Yoshikazu,Iwanaga, Kiyoshi,Yamamoto, Hisashi
, p. 6254 - 6255 (2007/10/02)
We chose α,β-unsaturated acids and investigated the reactivity of their borane adducts in Diels-Alder reactions.The reaction did proceed smoothly and has been found to be a useful method for synthesis of carboxylic acids.
