42710-26-9Relevant academic research and scientific papers
Cobalt-bisoxazoline-catalyzed asymmetric kumada cross-coupling of racemic α-bromo esters with aryl grignard reagents
Mao, Jianyou,Liu, Feipeng,Wang, Min,Wu, Lin,Zheng, Bing,Liu, Shangzhong,Zhong, Jiangchun,Bian, Qinghua,Walsh, Patrick J.
supporting information, p. 17662 - 17668 (2015/02/02)
The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt-bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. This method was conducted on gram-scale and applied to the synthesis of highly enantioenriched (S)-fenoprofen and (S)-ar-turmerone.
Enantioselective carbenoid insertion into phenolic O-H bonds with a chiral copper(I) imidazoindolephosphine complex
Osako, Takao,Panichakul, Duanghathai,Uozumi, Yasuhiro
supporting information; experimental part, p. 194 - 197 (2012/02/16)
The enantioselective O-H carbenoid insertion reaction with a new chiral copper(I) imidazoindolephosphine complex has been developed. The chiral copper(I) complex catalyzed the insertion of carbenoids derived from α-diazopropionates into the O-H bonds of various phenol derivatives to give the corresponding α-aryloxypropionates with up to 91% ee.
O-arylation of carboxylic acids using (phenyl)[2-(trimethylsilyl)phenyl] iodonium triflate as a precursor of arynes
Xue, Jian,Huang, Xian
, p. 2179 - 2185 (2008/02/05)
Using (phenyl)[2-(trimethylsilyl)phenyl]iodonium triflate as a precursor of arynes, Larock's method for O-arylation of carboxylic acids and arynes was developed. A variety of acids including simple aliphatic carboxylic acids, aromatic carboxylic acids, allenoic acids, and p-toluenesulfonic acid under mild reaction conditions could generate the aryl esters. Copyright Taylor & Francis Group, LLC.
Efficient radical oxygenation of α-lodocarboxylic acid derivatives
Kihara, Nobuhiro,Ollivier, Cyril,Renaud, Philippe
, p. 1419 - 1422 (2008/02/09)
(equation presented) Treatment of α-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding α-hydroxy add derivatives This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of riethylborane and oxygen, with the α-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimanation product is observed tertiary iodides are efficiently converted to alcohos, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.
Synthesis of substituted β-lactones by a Reformatsky reaction of carbonyl compounds, phenyl α-bromoalkanoates, and indium
Schick, Hans,Ludwig, Ralf,Kleiner, Katharina,Kunath, Annamarie
, p. 2939 - 2946 (2007/10/02)
Di-, tri-, and tetrasubstituted β-lactones are accessible in a one-step procedure by a Reformatsky reaction of phenyl α-bromoalkanoates with ketones or aldehydes at a sacrificial indium anode. With indium powder comparable results are obtained. The yield of β-lactones is significantly lower, if zinc is used instead of indium.
