19242-50-3Relevant articles and documents
BOROX catalysis: Self-assembled AMINO-BOROX and IMINO-BOROX chiral Bronsted acids in a five component catalyst assembly/ catalytic asymmetric aziridination
Gupta, Anil K.,Mukherjee, Munmun,Hu, Gang,Wulff, William D.
, p. 7932 - 7944,13 (2012)
A five-component catalyst assembly/aziridination reaction is described starting from an aldehyde, an amine, ethyl diazoacetate, B(OPh)3, and a molecule of a vaulted biaryl ligand (VAPOL or VANOL). A remarkable level of chemoselectivity was observed since, while 10 different products could have resulted from various reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only two other products could be detected in 3% yield. Studies reveal that the first in a sequence of three reactions is an exceedingly rapid amine-induced assembly of an AMINOBOROX chiral Bronsted acid species from VAPOL and B(OPh)3, which is followed by imine formation from the amine and aldehyde and the concomitant formation of an IMINO-BOROX chiral Bronsted acid and finally the reaction of the imine with ethyl diazoacetate mediated by the IMINO-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity.
Synthesis of vinyl and electron-deficient aryl trifluoromethyl sulfides via Csp2?OH bond activation with AgSCF3 and n-Bu4NI/KI
Liu, Yin-Li,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 5827 - 5832 (2018/09/21)
Direct dehydroxytrifluoromethylthiolation of enols and electron-deficient phenols with AgSCF3 in the presence of n-Bu4NI and KI is reported, affording a series of vinyl and aryl trifluoromethyl sulfides in moderate to excellent yields. This work represents a rare example of direct functionalization of Csp2?OH bonds.
Br?nsted acid mediated cyclizations of ortho-aryl(ethynyl)pyrimidines
Shestakov, Aleksandr N.,Pankova, Alena S.,Golubev, Pavel,Khlebnikov, Alexander F.,Kuznetsov, Mikhail A.
supporting information, p. 3939 - 3948 (2017/06/14)
A high-yielding procedure for the synthesis of 5-aryl-4-(arylethynyl)pyrimidines from easily available 2-aryl-3-hydroxyacrylates is reported. These pyrimidines readily undergo cyclization in strong Br?nsted acids and, depending on the substitution in alky