23985-58-2Relevant articles and documents
Asymmetric Diels-Alder, Michael, and aldol reactions using a planar chiral 1,3-oxazol-2(3H)-one derived from (R)-(+)-4-hydroxy-[2.2]paracyclophane
Cipiciani, Antonio,Fringuelli, Francesco,Piermatti, Oriana,Pizzo, Ferdinando,Ruzziconi, Renzo
, p. 2665 - 2670 (2002)
(+)-(R)-[2.2]Paracyclophane[4,5-d]-1,3-oxazol-2(3H)-one exhibiting planar chirality has been used as a chiral auxiliary in asymmetric Diels-Alder, Michael, and aldol reactions of α,β-unsaturated carboxy and enolate imides, respectively. The endo-exo- and face-diastereoselectivity is good and is controlled by the spatial relationship between the prochiral center and the C9-C10 ethylene bridge of the [2.2]paracyclophane moiety. The chiral auxiliary is easily removed and quantitatively recovered.
Opara,Read
, p. 679 (1969)
MNBA-mediated β-lactone formation: Mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin
Shiina, Isamu,Umezaki, Yuma,Kuroda, Nobutaka,Iizumi, Takashi,Nagai, Shunsuke,Katoh, Takashi
, p. 4885 - 4901 (2012/07/30)
Various β-lactones were prepared from β-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.
Rhenium-catalyzed reaction of carbonyl compounds with ketene silyl acetals
Nishiyama, Yutaka,Kaiba, Kenta,Umeda, Rui
experimental part, p. 793 - 795 (2010/03/24)
It was found that rhenium complex is an effective catalyst for the reaction of carbonyl compounds with ketene silyl acetals. A wide range of β-silyloxy esters is obtained by the treatment of carbonyl compounds with ketene silyl acetals in the presence of