Enantioselective Addition of Sodium Bisulfite to Nitroalkenes. A Convenient Approach to Chiral Sulfonic Acids

An enantioselective organocatalytic addition of sodium bisulfite to (E)-nitroalkenes has been developed by using a chiral bifunctional organocatalyst. The present methodology provides a variety of chiral beta-nitroethanesulfonic acid compounds (17 examples) with excellent results: up to 99 % yield and excellent enantioselectivity (up to 96 % ee). The reaction tolerates (hetero)aryl and alkyl substituents on the beta-nitroalkenes, and beta,beta-disubstituted nitroalkenes.

Automated summary

An enantioselective organocatalytic addition of sodium bisulfite to (E)-nitroalkenes has been developed using a chiral bifunctional organocatalyst, providing a variety of chiral beta-nitroethanesulfonic acid compounds. The reaction demonstrates high yield and excellent enantioselectivity under the reaction conditions.