Ring Opening of a Resin-Bound Chiral Aziridine with Phenols

Significance

The resin-bound chiral aziridine 3 was prepared from polystyrene trityl bromide resin 1 with (S)-N-nosylaziridine-2-methanol (2) and used for the synthesis of coumaryl amino acids via aziridine ring opening with phenolic nucleophiles. Thus, the ring opening of aziridines was carried out with 7-hydroxycoumarins 6a-c and t-BuOK to give the corresponding aryl alkyl ethers 7a-c, which were converted into the corresponding coumaryl amino acids 9a-c in four steps in 72-93% yield.