157944-16-6Relevant academic research and scientific papers
Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization
Kim, Jiyoung,Yoo, Eun Jeong
supporting information, p. 4256 - 4260 (2021/06/28)
Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.
Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement
Sha, Qiang,Arman, Hadi,Doyle, Michael P.
supporting information, p. 108 - 111 (2015/12/26)
An efficient two-step protocol for the asymmetric synthesis of 1H-pyrrol-3(2H)-one derivatives in 99% ee from conveniently accessed 2,3-diketoesters has been developed.
Copper(II)-acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters
Tayama, Eiji,Horikawa, Kouki,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information, p. 3041 - 3044 (2014/05/20)
Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with α-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters.
63. Enantioselective Formation of Bicyclic Lactones by Rhodium-Catalyzed Intramolecular CH-Insertion Reactions
Mueller, Paul,Polleux, Philippe
, p. 645 - 654 (2007/10/02)
The decomposition of cyclohexyl diazoacetate (5a) in the presence of the chiral 4> catalyst leads to a 3:1 cis/trans mixture of bicyclic lactone 6a with an enantiomeric excess of 95-97percent (cis) and 90percent (trans).The conformationally rigid tert-butyl derivatives 5b and 5c afford, in the presence of the same catalyst, 6b and 6c, respectively, via insertion into the equatorial C-H bonds exclusively, with ee's of ca. 95percent.A remarkable degree of induction (92-95percent) results in the lactone 6g upon decomposition of 1-isopropyl-2-methylpropyl diazoacetate (5g).The diazoacetates derived from 1-methylcyclohexanol, cyclopentanol and 1-methylcyclopentanol (5d-f) afford under similar conditions insertion products with higher diastereoselectivity, but significantly lower enantioselectivity.Other dirhodium catalysts are less efficient.
