Synthesis and Its Stereochemistry of Aminophosphonic Acids Derived From 5-Hydroxymethylfurfural

Rationalization of the stereochemistry of an addition of dialkyl phosphites to certain chiral aldimines: The experimental and theoretical approach

“…Unambiguous assignment of an absolute configuration of the ␣-P stereogenic center in isomers 3 (R = H [8] or CH 2 OH [5][6][7]9]) was necessary for a definitive explanation of the title process stereochemistry. Since the X-ray structure analysis could not be performed, the only method of configuration determination (i.e., omitting a derivatization technique) was computer modeling of the reliable geometry for both isomers under study.…”

“…It was demonstrated that such bisaddition to phenylene-bisimines is highly stereoselective though some exceptions were also noted [4]. In order to explain the mechanism of these reactions, we restudied our previous investigations on a single addition of phosphites to chiral Schiff bases [5][6][7], considering this as a model process.…”

“…An analysis of our case gave results confirming an initially proposed spatial aspect of the reaction mechanism. Therefore, we postulate that the chiral center in an ␣-P position of the predominant diastereomer of the 3a type (e.g., 3A) is in the R configuration [5][6][7].…”

“…Both products were separated by column chromatography and obtained as viscous liquids [5][6][7][8][9]. The stereochemistry of the process was initially interpreted [5,6] with the consideration that the predominant isomer 3a was formed in addition to an azomethine C N bond of a prochiral aldimine 1, which followed the general Cram model SCHEME 1 of stereoselectivity [10].…”

Multicomponent Reactions: A New Strategy for Enriching the Routes of Value-Added Conversions of Bio-platform Molecules

“…Skowronski 等 [35] [38] . 早 在 1984 年, Potts 等 [39] 以 2-糠醛二甲基腙和 N-乙基马来 酰亚胺为反应原料, 氯仿为溶剂, 通过串联的 Diels-Alder 环加成/芳构化反应合成得到一系列邻苯二甲酰亚 胺类衍生物(Eq.…”