1570-48-5Relevant articles and documents
Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light
Kyne, Sara Helen,Li, Jiacheng,Siang Tan, Suan,Wai Hong Chan, Philip
supporting information, (2022/01/11)
A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.
KETONE COMPOUND PRODUCTION PROCESS
-
Paragraph 0033; 0039; 0040, (2017/01/31)
PROBLEM TO BE SOLVED: To provide an industrially useful ketone compound production process that does not require, in the Corey-Kim oxidation reaction for oxidizing alcohol to ketone, the sulfide processing after the reaction. SOLUTION: There is provided the ketone compound production process in which, in a reaction for converting an alcohol compound represented by the following formula (II) to a ketone compound represented by the following formula (III) using a sulfide compound represented by the following formula (I) under the presence of a tertiary amine and a halogenation agent, the amount of use of the sulfide compound represented by the following formula (I) with respect to the alcohol compound represented by the following formula (II) is 0.3 to 0.95 mole equivalent. [R1 is a C1 to 18 alkyl group; R2 is a C2 to 18 alkyl group or an aryl group.]. [R3 is H, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic residue; R4 represents an alkyl group, an alkenyl group, an aryl group, or a heterocyclic residue; and the R3 and R4 may bond together and form a ring.]. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone
Ito, Masato,Kitahara, Sachiko,Ikariya, Takao
, p. 6172 - 6173 (2007/10/03)
Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-κ2-P,N]-KOt-Bu (Cp* = η5-C5(CH3)5) under mild conditions. Mechanistic consideration based on isotope-labeling experiments indicated the present reaction is applicable to the asymmetric isomerization of racemic sec-allylic alcohols with a prochiral olefin via dynamic kinetic resolution. A concise asymmetric synthesis of muscone has been achieved, where the asymmetric isomerization using an optically active ligand is a key reaction. Copyright
