Highly enantio- and diastereoselective vicinal chloro- and iodoamination reaction of enecarbamates catalyzed by chiral phosphoric acids or chiral calcium organophosphates are reported. The approach described herein provides efficient access to cis-chloro and cis-iodoaminals in good yields and excellent enantioselectivities (up to 99% ee). The resulting products are converted readily into highly important trans-azidoaminals.
Key words
chiral phosphoric acid - chiral calcium phosphate - haloamination - enecarbamate - intermolecular difunctionalization - organocatalysis