61712-12-7Relevant academic research and scientific papers
(E)- and (Z)-stereodefined enol phosphonates derived from β-ketoesters: Stereocomplementary synthesis of fully-substituted α,β-unsaturated esters
Nakatsuji, Hidefumi,Ashida, Yuichiro,Hori, Hiroshi,Sato, Yuka,Honda, Atsushi,Taira, Mayu,Tanabe, Yoo
, p. 8205 - 8210 (2015/08/03)
A versatile, robust, and stereocomplementary synthesis of fully-substituted (E)- and (Z)-stereodefined α,β-unsaturated esters 3 from accessible α-substituted β-ketoesters 1via (E)- and (Z)-enol phosphonates was achieved. The present method involves two ac
Catalytic enantioselective nazarov cyclization: Construction of vicinal all-carbon-atom quaternary stereocenters
Jolit, Anais,Walleser, Patrick M.,Yap, Glenn P. A.,Tius, Marcus A.
, p. 6180 - 6183 (2014/06/23)
The diastereoselective asymmetric synthesis of vicinal all-carbon-atom quaternary stereocenters is a challenging problem in organic synthesis for which only few solutions have been described. A catalytic asymmetric Nazarov cyclization of fully substituted dienones that provides cyclopentenone derivatives with vicinal quaternary stereocenters in high optical purity and as single diastereoisomers is now reported.
Tandem Blaise/retro-Blaise reaction for the nitrile-mediated regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky Reagents) to 1-alkynes and 1,3-enynes
Kim, Ju Hyun,Chun, Yu Sung,Lee, Sang-Gi
, p. 11483 - 11493 (2013/12/04)
We report the novel use of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1-alkynes and 1,3-enynes. This reaction is made possible by a reversible addition of enolates to a nitrile (Blaise reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1,3-enynes. Subsequent removal of the nitrile through a retro-Blaise reaction generates the targeted addition product. This method is combined with a Diels-Alder reaction and subsequent oxidative aromatization, providing a tandem one-pot de novo construction of α-arylated alkanoates from Reformatsky reagents.
Intramolecular Diels-Alder Cycloadditions of Perchloro(allyloxy)- and Perchlorobis(allyloxy)cyclopentadienes
Jung, Michael E.,Light, Lynn A.
, p. 1084 - 1090 (2007/10/02)
The intramolecular cycloadditions of some mono(allyloxy)- and bis(allyloxy)perchlorocyclopentadienes have been carried out.Even in the case of trisubstituted olefins, this internal cycloaddition process occurs in good yield.The allyloxy compounds (10, 11,
SYNTHESIS, MOLECULAR PROPERTIES AND PHARMACOLOGICAL ACTIVITY OF SOME p-SUBSTITUTED (E)- AND (Z)-α,β-DIMETHYLCINNAMIC ACIDS
Balsamo, Aldo,Crotti, Paolo,Macchia, Bruno,Macchia, Franco,Martinelli, Adriano,et al.
, p. 327 - 332 (2007/10/02)
A series of p-substituted (E)- and (Z)-α,β-dimethylcinnamic acids has been prepared and pharmacologically tested.The configurations of the acids prepared were determined from their NMR spectra.The UV spectra and the acid dissociation constants are reported.The collected data show that an extensive conjugation between the aryl and carboxy groups via the double bond does not exist, due to the steric hindrance of the α,β-dimethyl substitution on the cinnamic system.
