1001615-58-2Relevant academic research and scientific papers
Palladium-Catalyzed Hydrocarbonylative Cyclization of 1,5-Dienes
Zou, Suchen,Gao, Bao,Huang, Yao,Zhang, Tianze,Huang, Hanmin
supporting information, p. 6333 - 6336 (2019/08/26)
A novel and atom-economic palladium-catalyzed isomerization-hydrocarbonylative cyclization reaction of 1,5-dienes to 2-alkylidenecyclopentanones has been developed, which provides a rapid and straightforward approach to 2-alkylidenecyclopentanones with high stereoselectivity. The reaction was found to proceed via alkene isomerization and selective hydrocarbonylative cyclization to generate 2-alkylidenecyclopentanones with high selectivity.
Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization
Usami, Kaoru,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 5714 - 5717 (2018/09/21)
The treatment of an O-(4-methoxybenzyl) oxime ether bearing an olefin substituent and 1-chloroanthraquinone (1-Cl-AQN) catalyst in 2-butanone under visible-light irradiation affords pyrroline via an iminyl radical intramolecular hydroimination. Mechanistic studies indicate that iminyl radical generation mainly proceeds by hydrogen abstraction of the photocatalyst from the benzyl position of the oxime. Moreover, the hydrogen atom was identified in circulation from the benzylic position of the substrates between AQN and 2-butanone to quench the carbon radical without requiring any additional reagents.
Oxidative cyclization of tertiary pentenol derivatives forming 2,5,5-trisubstituted THF rings and the total synthesis of cyclocapitelline
Phillips, Geoffrey A.,Palmer, Cory,Stevens, Andrew C.,Piotrowski, Mathew L.,Dekruyf, Daryl S.R.,Pagenkopf, Brian L.
supporting information, p. 6052 - 6055 (2015/10/28)
The synthesis of 2,5,5-trisubstituted tetrahydrofuran rings was accomplished via the Mukaiyama aerobic oxidative cyclization of tertiary 5-pentenols employing the Co(nmp)2 catalyst. A variety of THFs were formed in moderate to good yield and diastereoselectivity. The method developed herein was successfully applied to an enantioselective total synthesis of cyclocapitelline.
Pd-catalyzed domino carbonylative-decarboxylative allylation: An easy and selective monoallylation of ketones
Giboulot, Steven,Liron, Frederic,Prestat, Guillaume,Wahl, Benoit,Sauthier, Mathieu,Castanet, Yves,Mortreux, Andre,Poli, Giovanni
supporting information; experimental part, p. 5889 - 5891 (2012/07/28)
In the presence of an allyl alcohol, α-chloroacetophenones undergo an allyloxycarbonylation reaction followed by in situ decarboxylative allylation to selectively afford the corresponding monoallylated ketones via a Pd-catalyzed domino sequence. The scope of the reaction was extended to substituted α-chloroacetophenones as well as various allyl alcohols.
Dimerization and isomerization reactions of α-lithiated terminal aziridines
Hodgson, David M.,Humphreys, Philip G.,Miles, Steven M.,Brierley, Christopher A. J.,Ward, John G.
, p. 10009 - 10021 (2008/03/28)
(Chemical Equation Presented) The scope of dimerization and isomerization reactions of α-lithiated terminal aziridines is detailed. Regio-and stereoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (LTMP) or lithium dicyclohexylamide (LiNCy 2) generates trans-α-lithiated terminal aziridines. These latter species can then undergo dimerization or isomerization reactions depending on the nature of the N-protecting group. α-Lithiated terminal aziridines bearing N-alkoxycarbonyl (Boc) protection undergo N- to C-[1,2] migration to give N-H trans-aziridinylesters. In contrast, aziridines bearing N-organosulfonyl [tert-butylsulfonyl (Bus)] protection undergo rapid dimerization to give 2-ene-1,4-diamines or, if a pendant alkene is present, diastereoselective cyclopropanation to give 2-aminobicyclo[3.1.0]hexanes. All of these reactions were used as key steps in the preparation of synthetically and biologically important targets.
Free radical trapping of α-keto radicals derived from α,β-epoxy ketones via photoinduced single electron transfer process
Hasegawa, Eietsu,Ishiyama, Kenyuki,Horaguchi, Takaaki,Shimizu, Takahachi
, p. 2029 - 2032 (2007/10/02)
Irradiation of aromatic α,β-epoxy ketones in the presence of allyltributyltin afforded α-allyl-β-hydroxy ketones by a single electron transfer mechanism.
