22573-51-9Relevant academic research and scientific papers
Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst
Gavin, Declan P.,Murphy, Edel J.,Foley, Aoife M.,Castilla, Ignacio Abreu,Reen, F. Jerry,Woods, David F.,Collins, Stuart G.,O'Gara, Fergal,Maguire, Anita R.
, p. 2466 - 2474 (2019/03/11)
Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).
Enantioselective Hydrogenation of β,β-Disubstituted Unsaturated Carboxylic Acids under Base-Free Conditions
Yan, Qiaozhi,Kong, Duanyang,Zhao, Wei,Zi, Guofu,Hou, Guohua
, p. 2070 - 2077 (2016/03/15)
An additive-free enantioselective hydrogenation of β,β-disubstituted unsaturated carboxylic acids catalyzed by the Rh-(R,R)-f-spiroPhos complex has been developed. Under mild conditions, a wide scope of β,β-disubstituted unsaturated carboxylic acids were hydrogenated to the corresponding chiral carboxylic acids with excellent enantioselectivities (up to 99.3% ee). This methodology was also successfully applied to the synthesis of the pharmaceutical molecule indatraline.
Asymmetric syntheses and bio-evaluation of novel chiral esters derived from substituted tetrafluorobenzyl alcohol
Xu, Shengzhen,Li, Huangyong,Wang, Xiaohui,Chen, Changshui,Cao, Minhui,Cao, Xiufang
supporting information, p. 2734 - 2736 (2015/02/19)
A series of novel chiral esters derived from tetrafluorobenzyl alcohol were designed and prepared via asymmetric synthesis. The target molecules have been identified on the basis of analytical spectra data. All newly synthesized compounds have been screened their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and d-trans-phenothrin by standard method, and the respective pairs of enantiomers (3-B1-R/S, 3-C1-R/S, 3-D1-R/S) indicated significantly different activities.
Asymmetric syntheses and bio-evaluation of novel chiral esters derived from substituted tetrafluorobenzyl alcohol
Xu, Shengzhen,Li, Huangyong,Wang, Xiaohui,Chen, Changshui,Cao, Minhui,Cao, Xiufang
supporting information, p. 2734 - 2736 (2014/06/09)
A series of novel chiral esters derived from tetrafluorobenzyl alcohol were designed and prepared via asymmetric synthesis. The target molecules have been identified on the basis of analytical spectra data. All newly synthesized compounds have been screened their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and d-trans-phenothrin by standard method, and the respective pairs of enantiomers (3-B1-R/S, 3-C1-R/S, 3-D1-R/S) indicated significantly different activities.
Lipase catalysed kinetic resolutions of 3-aryl alkanoic acids
Deasy, Rebecca E.,Brossat, Maude,Moody, Thomas S.,Maguire, Anita R.
, p. 47 - 61 (2011/04/18)
Hydrolase catalysed kinetic resolutions leading to a series of 3-aryl alkanoic acids (≥94% ee) are described. Hydrolysis of the ethyl esters with a series of hydrolases was undertaken to identify biocatalysts that yield the corresponding acids with excellent enantiopurity in each case. Steric and electronic effects on the efficiency and enantioselectivity of the biocatalytic transformation were also explored.
Chiral Lewis acid catalyzed enantioselective conjugate radical additions to α,β-unsaturated 2-pyridyl ketones
Sibi, Mukund P.,Yang, Yong-Hua
, p. 83 - 88 (2008/09/21)
We have investigated the utility of a pyridine-based achiral template in enantioselective conjugate radical additions. Georg Thieme Verlag Stuttgart.
Enantioselective conjugate radical addition to α′-hydroxy enones
Lee, Sunggi,Chae, Jo Lim,Kim, Sunggak,Subramaniam, Rajesh,Zimmerman, Jake,Sibi, Mukund P.
, p. 4311 - 4313 (2007/10/03)
(Chemical Equation Presented) Enantioselective conjugate radical addition to α′-hydroxy α,β-unsaturated ketones, compounds containing bidentate donors, has been investigated. It has been found that radical additions to α′-hydroxy α,β-unsaturated ketones i
Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters
Takaya, Yoshiaki,Senda, Taichi,Kurushima, Hiroaki,Ogasawara, Masamichi,Hayashi, Tamio
, p. 4047 - 4056 (2007/10/03)
Reaction of arylboron reagents, arylboronic acids or arylborates, which are readily accessible by lithiation of aryl bromides followed by treatment with trimethoxyborane, with α,β-unsaturated esters in the presence of rhodium/(S)-binap catalyst proceeded with high enantioselectivity to give high yields of optically active β-aryl esters of up to 98% ee. The enantioselectivity depends on the steric bulkiness of the ester moiety.
Free radical-mediated intermolecular conjugate additions. Effect of the lewis acid, chiral auxiliary, and additives on diastereoselectivity
Sibi, Mukund P.,Ji, Jianguo,Sausker, Justin B.,Jasperse, Craig P.
, p. 7517 - 7526 (2007/10/03)
We have developed a highly diastereoselective method for the conjugate addition of carbon radicals to chiral α,β-unsaturated N-enoyloxazolidinones using Bu3SnH as chain carrier and Et3B/O2 as radical initiator. Lewis acids
Enantioselective intermolecular free radical conjugate additions. Application of a pyrazole template
Sibi, Mukund P.,Shay, John J.,Ji, Jianguo
, p. 5955 - 5958 (2007/10/03)
An achiral pyrazole template has been evaluated in enantioselective conjugate radical additions. The enantioselectivity using the pyrazole template is inferior to those obtained from an oxazolidinone template. The two templates give products of opposite c
