1383003-37-9Relevant academic research and scientific papers
Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel–Crafts Conjugate Addition of Indolizines
Ni, Qijian,Zhu, Zhiming,Fan, Yanjun,Chen, Xiaoyun,Song, Xiaoxiao
, p. 9548 - 9553 (2021/12/14)
An organocatalytic highly diastero- and enantioselective Friedel–Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62–91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp2 C–H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.
Silver-Catalyzed Asymmetric Desymmetrization of Cyclopentenediones via [3 + 2] Cycloaddition with α-Substituted Isocyanoacetates
George, Jimil,Kim, Hun Young,Oh, Kyungsoo
, p. 2249 - 2252 (2018/04/30)
A highly selective and practical asymmetric Ag(I) catalyst system has been developed for the [3 + 2] cycloaddition reactions between isocyanoacetates and cyclopentenediones. The current Ag(I) catalyst system tolerates moisture and air and readily utilizes class III solvents such as EtOAc and acetone. The development of on demand generation of an active chiral catalyst in the presence of isocyanides paves a way to the efficient asymmetric preparation of bicyclic pyrrolidines with four stereogenic centers, including two quaternary centers in 80-97% ee.
Oxidative Heck desymmetrisation of 2,2-disubstituted cyclopentene-1,3-diones
Walker,Lamb,Beattie,Nikodemiak,Lee
supporting information, p. 4089 - 4092 (2015/03/30)
Oxidative Heck couplings have been successfully developed for 2,2-disubstituted cyclopentene-1,3-diones. The direct coupling onto the 2,2-disubstituted cyclopentene-1,3-dione core provides a novel expedient way of enantioselectively desymmetrising all-carbon quaternary centres. This journal is
Copper(I)-catalyzed asymmetric desymmetrization: Synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters
Aikawa, Kohsuke,Okamoto, Tatsuya,Mikami, Koichi
supporting information; experimental part, p. 10329 - 10332 (2012/07/30)
A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with excellent stereoselectivities using a low catalyst loading in a one-pot operation.
