873695-73-9Relevant academic research and scientific papers
Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Br?nsted Acid Catalyst
Hatano, Manabu,Nishikawa, Keisuke,Ishihara, Kazuaki
, p. 8424 - 8427 (2017/07/06)
A chiral magnesium potassium binaphthyldisulfonate cluster, as a chiral Br?nsted acid catalyst, was shown to catalyze an enantioselective cycloaddition of styrenes with aldimines for the first time. The strong Br?nsted acidity of the catalyst precursors,
Asymmetric reduction of racemic 2-isoxazolines
Tokizane, Masashi,Sato, Kaori,Ohta, Tetsuo,Ito, Yoshihiko
scheme or table, p. 2519 - 2528 (2009/04/04)
The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-α,α-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered substrates.
Asymmetric aza-Mannich reactions of sulfinimines: Scope and application to the total synthesis of a bromopyrrole alkaloid
Lanter, James C.,Chen, Hongfeng,Zhang, Xuqing,Sui, Zhihua
, p. 5905 - 5907 (2007/10/03)
(Chemical Equation Presented) An asymmetric intermolecular aza variant of the Mannich reaction is reported utilizing chiral sulfinimine anions as the nucleophile and N-sulfonyl aldimines as the electrophilic component. A wide range of nucleophiles and ele
