141036-66-0Relevant articles and documents
Development of a robust immobilized organocatalyst for the redox-neutral mitsunobu reaction
Lai, Junshan,Llanes, Patricia,Mastandrea, Marco M.,Pericàs, Miquel A.,Perulli, Stefania,Zhou, Leijie
supporting information, p. 8859 - 8864 (2021/11/23)
A polystyrene-supported version of the Denton catalyst for redox-neutral Mitsunobu reactions, (2-hydroxybenzyl)diphenylphosphine oxide, has been developed and used in catalytic inversion of enantiopure secondary alcohols (21 examples, up to 97% yield and 98% ee) with 2-nitrobenzoic and 2,4-dinitrobenzoic acids. The use in the reaction of alternative pronucleophiles has also been explored (8 successful and 3 unsuccessful examples). The functional resin shows high recyclability (10 cycles, 30 days operation) and can be re-activated by simple treatment with butylamine with further extension of its useful life.
A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols
Lin, Hui,Tang, Yanhong,Dong, Shuang,Lang, Ruibo,Chen, Hongge
, p. 2145 - 2151 (2020/04/17)
Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six st
A General Diastereoselective Strategy for Both cis- and trans-2,6-Disubstituted Tetrahydropyrans: Formal Total Synthesis of (+)-Muconin
Srinivas, Beduru,Reddy, D. Srinivas,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.
supporting information, p. 6910 - 6914 (2018/11/02)
A protocol for general diastereoselective tandem dihydroxylation followed by SN2 cyclization was developed for the convenient and efficient synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans from ζ-mesyloxy α,β-unsaturated esters. T
Copper(I)-catalyzed enantioselective nucleophilic borylation of aldehydes: An efficient route to enantiomerically enriched α-alkoxyorganoboronate esters
Kubota, Koji,Yamamoto, Eiji,Ito, Hajime
supporting information, p. 420 - 424 (2015/01/30)
The first catalytic enantioselective nucleophilic borylation of a
Asymmetric epoxidation of alkenes and benzylic hydroxylation with P450tol monooxygenase from Rhodococcus coprophilus TC-2
Li, Aitao,Wu, Shuke,Adams, Joseph P.,Snajdrova, Radka,Li, Zhi
supporting information, p. 8771 - 8774 (2014/07/22)
P450tol monooxygenase was discovered as a unique and highly enantioselective enzyme for asymmetric epoxidation of some terminal alkenes containing electron-withdrawing groups and benzylic hydroxylation of several ethylbenzenes giving the corresponding useful and valuable products, such as (R)-2- and 3-substituted styrene oxides, (S)-4-substituted styrene oxides, and (S)-benzylic alcohols, in high ee.
Gold(I)-Catalyzed access to tetrahydropyran-4-ones from 4-(Alkoxyalkyl)oxy-1-butynes: Formal catalytic petasis-ferrier rearrangement
Bae, Hyo Jin,Jeong, Wook,Lee, Ji Hyung,Rhee, Young Ho
supporting information; experimental part, p. 1433 - 1436 (2011/04/12)
Gold cycle redesigned: By utilizing the alkynophilic effect of gold(I) complexes, a new method for the synthesis of highly substituted cis-2,6-tetrahydropyranones was developed, which represents a catalytic surrogate of the Petasis-Ferrier rearrangement (
Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(o-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization
Kurosaki, Yuji,Fukuda, Tsutomu,Iwao, Masatomo
, p. 3289 - 3303 (2007/10/03)
Lateral lithiation of (S)-4-isopropyl-2-(o-tolyl)oxazoline in diethyl ether followed by the reaction with aldehydes in the presence of TMEDA produced the addition products with stereoselectivities up to 84% de. Utilization of TMEDA as a ligand is essential for the good selectivity. Rationale for the stereoselectivity is proposed based on ab initio calculation of the lateral lithio species. The major (S,S)-products lactonized faster than the minor (S,R)-products to the corresponding 3,4-dihydroisocoumarins under acidic conditions. Thus, (3S)-3,4-dihydroisocoumarins were obtained in good optical purities up to 97% ee by sequential application of these matched stereoselective reactions.
Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors
Kim, Choung U.,Lew, Willard,Williams, Matthew A.,Wu, Huiwei,Zhang, Lijun,Chen, Xiaowu,Escarpe, Paul A.,Mendel, Dirk B.,Laver, W. Graeme,Stevens, Raymond C.
, p. 2451 - 2460 (2007/10/03)
A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized and evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.
A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF CHIRAL MONOSUBSTITUTED OXIRANES
Corey, E. J.,Helal, Christopher J.
, p. 5227 - 5230 (2007/10/02)
A new catalytic enentioselective synthesis of monosubstituted oxiranes has been developed from achiral trichloromethyl ketones by (a) enentioselective carbonyl reduction, (b) selective bis-dechlorination and (c) base-induced ring closure of the resulting chlorohydrins.
Asymmetric Synthesis of (-) (R) Yashabushiketol
Solladie, Guy,Ziani-Cherif, Chewki,Jesser, Francis
, p. 931 - 934 (2007/10/02)
(-)(R) Yashabushiketol was prepared from the epoxide 4 readily available in both configurations by reduction of β-ketosulfoxides.
