Straightforward Diastereoselective Synthesis of P-Chirogenic (1R)-1,8,8-Trimethyl-2,4-diaza-3-phosphabicyclo[3.2.1]octane 3-Oxides: Application as Chiral NMR Solvating Agents

Abstract

A direct route to enantio- and diastereopure nitrogen-substituted phosphine oxides has been developed. The desired P-stereogenic compounds were obtained in good yields and high purity. The starting point of the synthesis was (+)-camphor, which is a readily available compound from the chiral pool. The new nitrogen-substituted phosphine oxides could be transformed from their pentavalent state to their trivalent form with N,O-bis(trimethylsilyl)acetamide, which makes them potential chiral ligands. It was possible to apply these compounds as chiral-solvating agents in chiral recognition experiments with a racemic alcohol and acid.