Novel One‐Pot Access to Diastereoisomeric Tertiary Phospholanes Oxides by Using Enantiomerically Pure Phospholane Oxides Under Catalyst‐Free Conditions

Abstract

For the first time, enantiopure 1‐r‐oxo‐2‐c,5‐t‐diphenylphospholane was introduced as nucleophile in the multicomponent condensation reaction. Diastereoisomers of 2,5‐diphenyl‐1‐oxo‐1‐[alkylphenyl‐1‐(phenylamino) methyl] phospholane derivatives were synthesized by one‐pot process from aromatic aldehydes, anilines and enantiopure1‐r‐oxo‐2‐c,5‐t‐diphenylphospholane under green and eco‐compatible conditions. The reaction proceeds under catalyst‐free conditions at room temperature within very short time (3 min) in excellent yields (up to 95%). An X‐ray crystal structure has been obtained for 2,5‐diphenyl‐1‐oxo‐1‐[phenyl (phenylamino) methyl] phospholane.

Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives

“…P(O),NH-acetals, obtained by 3C-phospha-Mannich reactions of primary amines with SPOs and carbonyl compounds. [87] 2 Indium complex SF, r.t., 6 h 94 [88] Indium complex SF, r.t., 6 h 96 [88] AgSbF6 SF, r.t., 6 h 94 [89] 3 Indium complex SF, r.t., 6 h 98 [88] 4 Indium complex SF, r.t., 6 h 96 [88] AgSbF6 SF, r.t., 6 h 92 [89] AgSbF6 SF, r.t., 6 h 87 [89] 5 Indium complex SF, r.t., 6 h 98 [88] 6 Indium complex SF, r.t., 6 h 98 [88] AgSbF6 SF, r.t., 6 h 94 [89] 7 Indium complex SF, r.t., 6 h 86 [88] 8 Indium complex SF, r.t., 6 h 95 [88] AgSbF6 SF, r.t., 6 h 92 [89] 9 Indium complex SF, r.t., 6 h 92 [88] 10…”

“…P(O),NH-acetals, obtained by reaction of 2,5-diphenylphospholane 1-oxide with anilines and aromatic aldehydes. [87] S 94…”

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

“…Organophosphorus encompasses various compounds containing carbone-phosphore bond such as α-aminophosphonic acids and their esters α-aminophosphonates, [1][2][3][4] αaminophosphates [5][6] phosphinates and phosphine oxides, [7] αhydrazinophosphonic acid. [8] Amongst the entire organophosphonrus, the α-aminophosphonates analogues of aminocarboxylic acids, possess an important class in biological and therapeutic domains because of their low toxicity.…”