6533b85ffe1ef96bd12c271e

RESEARCH PRODUCT

Enantioselective addition of sodium bisulfite to nitroalkenes. A convenient approach to chiral sulfonic acids

Amparo Sanz-marcoCarlos VilaM. Carmen MuñozNarjes RezaeiAlvaro CastillaEhsan SheikhiJosé R. PedroGonzalo Blay

subject

chemistry.chemical_classificationchemistry.chemical_compoundchemistryCatàlisiSodium bisulfiteOrganocatalysisOrganic ChemistryEnantioselective synthesisOrganic chemistryPhysical and Theoretical ChemistrySulfonic acidQuímica orgànica

description

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 β-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 β-nitroalkenes, and β,β-disubstituted nitroalkenes.

yearjournalcountryeditionlanguage
2021-10-04
10.1002/ejoc.202101064https://hdl.handle.net/10550/80414