10521-91-2Relevant articles and documents
Reactions of triflate esters and triflamides with an organic neutral super-electron-donor
Jolly, Phillip I.,Fleary-Roberts, Nadia,O'Sullivan, Steven,Doni, Eswararao,Zhou, Shengze,Murphy, John A.
, p. 5807 - 5810 (2012)
The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively, using DMF as solvent, generally in excellent yields. While the deprotection of aryl triflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18O labelled DMF indicate that the C-O bond stays intact and hence it is the S-O bond that cleaves, underlining that the cleavage results from the extraordinary electron donor capability of 13. Trifluoromethanesulfonamides are converted to the parent amines in like manner, representing the first cleavage of such substrates by a ground-state organic reducing reagent.
Development of a potent 2-oxoamide inhibitor of secreted phospholipase A2 guided by molecular docking calculations and molecular dynamics simulations
Vasilakaki, Sofia,Barbayianni, Efrosini,Leonis, Georgios,Papadopoulos, Manthos G.,Mavromoustakos, Thomas,Gelb, Michael H.,Kokotos, George
, p. 1683 - 1695 (2016)
Inhibition of group IIA secreted phospholipase A2 (GIIA sPLA2) has been an important objective for medicinal chemists. We have previously shown that inhibitors incorporating the 2-oxoamide functionality may inhibit human and mouse GIIA sPLA2s. Herein, the development of new potent inhibitors by molecular docking calculations using the structure of the known inhibitor 7 as scaffold, are described. Synthesis and biological evaluation of the new compounds revealed that the long chain 2-oxoamide based on (S)-valine GK241 led to improved activity (IC50 = 143 nM and 68 nM against human and mouse GIIA sPLA2, respectively). In addition, molecular dynamics simulations were employed to shed light on GK241 potent and selective inhibitory activity.
Epoxide Electroreduction
Huang, Cheng,Lu, Qingquan,Ma, Wan,Qi, Xiaotian,Xu, Minghao,Zheng, Xuelian
supporting information, p. 1389 - 1395 (2022/01/19)
Selective hydrogenation of epoxides would be a direct and powerful approach for alcohol synthesis, but it has proven to be elusive. Here, electrochemically epoxide hydrogenation using electrons and protons as reductants is reported. A wide range of primary, secondary, and tertiary alcohols can be achieved through selective Markovnikov or anti-Markovnikov ring opening in the absence of transition metals. Mechanistic investigations revealed that the regioselectivity is controlled by the thermodynamic stabilities of the in situ generated benzyl radicals for aryl-substituted epoxides and the kinetic tendency for Markovnikov selective ring opening for alkyl-substituted epoxides.
Selective hydroboration of equilibrating allylic azides
Liu, Ruzhang,Xu, Jun,Zhang, Yuanyuan
supporting information, p. 8913 - 8916 (2021/09/13)
The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.
Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes
Kuhwald, Conrad,Kirschning, Andreas
supporting information, p. 4300 - 4304 (2021/05/26)
The Matteson reaction is ideally suited for flow chemistry since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative workup. The new terpene alcohols are validated with respect to their olfactoric properties.
