67516-83-0Relevant academic research and scientific papers
Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents
Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Zhang, Dong,Zhang, Fengcai
supporting information, p. 6961 - 6966 (2021/09/11)
An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.
Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes
Luo, Wenping,Fang, Yewen,Zhang, Li,Xu, Tianhang,Liu, Yongjun,Li, Yan,Jin, Xiaoping,Bao, Jiakan,Wu, Xiaodong,Zhang, Zongyong
supporting information, p. 1778 - 1781 (2020/03/11)
A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.
Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ
Jiang, Shan-Shan,Gu, Bo-Qi,Zhu, Ming-Yu,Yu, Xingxin,Deng, Wei-Ping
, p. 1187 - 1191 (2015/02/19)
Chiral α-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic α-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer
Synthesis of pyrazolines by a site isolated resin-bound reagents methodology
Gembus, Vincent,Bonnet, Jean-Jacquesrouen,Janin, Franoisrouen,Bohn, Pierre,Levacher, Vincent,Briere, Jean-Franois
supporting information; experimental part, p. 3287 - 3293 (2010/08/21)
The elaboration of biologically important 3,4-substituted pyrazolines was achieved by an organocatalysed aza-Michael/transimination domino sequence between hydrazones and enones making use of a mixture of heterogeneous resin-bound acid/base reagents. This methodology nicely illustrates the site isolation concept of supported reagents allowing the simultaneous use of otherwise destructive reactive functionalities. The Royal Society of Chemistry 2010.
Remote stereocontrol mediated by a sulfinyl group: Synthesis of allylic alcohols via chemoselective and diastereoselective reduction of γ-methylene δ-ketosulfoxides
Ruano, Jose L. Garcia,Fernandez-Ibanez, M. Angeles,Fernandez-Salas, Jose A.,Maestro, M. Carmen,Marquez-Lopez, Pablo,Rodriguez-Fernandez, M. Mercedes
supporting information; scheme or table, p. 1200 - 1204 (2009/07/18)
The efficiency of the sulfinyl group as a remote controller of the chemoselectivity and diastereoselectivity of the reduction of α,β-unsaturated α-[2-(p-tolylsulfinyl)phenyl] substituted ketones 1 has been demonstrated in reactions carried out under NaBH
Aziridination of 2- and 3-phenyl-substituted allylic alcohols with 3-acetoxyaminoquinazolinones: Probing the nature of the transition state from the diastereoselectivity of aziridination
Atkinson, Robert S.,Ulukanli, Sabri,Williams, Paul J.
, p. 2121 - 2128 (2007/10/03)
Aziridination of phenyl-substituted allylic alcohol 10 with 3-acetoxyaminoquinazolinone 3 (Q'NHOAc) and with 22 (Q2NHOAc) has been studied. The diastereoselectivity of these reactions is markedly changed by carrying them out in the presence of aqueous sodium hydrogen carbonate solution and under these conditions aziridinations of 10 and of its ester analogue 5 with Q2NHOAc give the same magnitude and sense of diastereoselectivity (with Ph=CO2Me). An explanation for these changes in diastereoselectivity is offered based upon differences in the nature of the hydrogen bonding in the transition states for aziridination of 10 with and without the presence of acetic acid.
