Facile and Efficient Asymmetric Synthesis ofα-Aminoalkylphosphonic Acids

Abstract

An improved procedure for the asymmetric synthesis of α‐aminoalkylphosphonic acids using S‐2‐anilino‐methylpyrrolidine as the chiral auxiliary was described. The chemical transformations involved in this protocol could proceed under mild reaction condition to provide good chemical and enantiomeric yields.

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

“…Methyl iodide was chosen to alkylate pseudo‐enolate, thus forming compound 71 a , which can be treated with 1 M HCl solution to yield l ‐Ala(P) with high enantiomeric excess. Another example of asymmetric synthesis of l ‐Ala(P) was presented by Yuan et al [96] . ( S )‐2‐Anilinomethylpyrrolidine 72 was used as a chiral auxiliary (Scheme 10, path B).…”

“…Another example of asymmetric synthesis of l ‐Ala(P) was presented by Yuan et al . [96] ( S )‐2‐Anilinomethylpyrrolidine 72 was used as a chiral auxiliary (Scheme 10 , path B). After separation of diastereoisomers 73 , optically pure compound 71 b was transformed into l ‐Ala(P) in a similar way.…”

Sequential Deprotonation–Alkylation of Binaphthyloxy-Substituted Phosphonochalcogenoates: Chiral Tri- and Tetrasubstituted Carbon Centers Adjacent to a Phosphorus Atom

“…Alternatively, the use of chiral auxiliaries is a reliable method to control the stereochemistry of the reaction of carbanions, whereby the judicious choice of chiral auxiliary is crucial. In fact, optically active 1,2-aminoalcohol-, 1,2-diamine-, and menthyl-tethered phosphonates have been used as precursors for chiral organophosphorus compounds such as I . However, even with these established methods, the construction of chiral centers substituted with only simple alkyl groups next to the phosphorus atom remains a challenging task.…”