ChemInform Abstract: Synthesis of New Furan‐Derived N‐Substituted Aminomethanephosphonates.

Abstract

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Stereochemical aspects of the hypophosphorous acid addition to terephthalic schiff bases. Synthesis of new 1,4‐phenylene‐bis‐aminomethane‐bis‐phosphonous acids

“…However, it was proven in papers [2][3][4][5][6][7][8][9][10] that the addition of dialkyl or diaryl phosphites to N-alkyl terephthalic Schiff bases led to the exclusive formation of one diastereoisomeric form. Our previous study [6][7][8][9] revealed that this diastereoisomer was the meso form. On the other hand, the addition of dialkyl or diaryl phosphites to N-aryl terephthalic Schiff bases led exclusively either to the formation of the meso form or to both diastereomeric forms, which depended on the nature of the aryl substituent [8,9].…”

“…Later papers authored by Finocchiaro et al [2][3][4] and Gancarz et al [5] presented the discussion on the stereochemical aspect of these reactions. Our group has also contributed to this topic reporting about the stereochemistry of addition reactions to various N-substituted terephthalic imines [6][7][8][9]. A comprehensive and detailed report on NMR spectroscopic and molecular modeling studies of 1,4-phenylene-bis-aminomethane-bisphosphonates and related structures is given in [10].…”

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

“…Using this methodology, we recently obtained some phenylene-bisaminomethanephosphonates, and an unusual stereochemical outcome of these reactions was pointed out. 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.…”