Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 37, Pages 5284-5287Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101064
Keywords
Asymmetric catalysis; Conjugate addition; Nitroalkenes; Organocatalysis; Sulfonic acid
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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.
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.
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