A valuable strategy for the construction of chiral amines is the enantioselecitve conjugate addition of nucleophiles to nitroalkenes. Despite the large body of literature on these reactions, enantioselective additions to α-substituted nitroalkenes remain sparse due to the challenge of setting the nitroalkane stereocenter. Using urea hydrogen bonding organocatalysts, carbon and sulfur nucleophiles have been added to α,β,β-trisubstituted nitroalkenes to furnish densely substituted chiral nitroalkanes with high fidelity. A key feature of this chemistry is the use of an enantioselective protonation strategy to set the nitroalkane stereocenter by means of facial selective protonation of a nitronate intermediate.

Enantioselective organocatalytic addition of carbon and sulfur nucleophiles to trisubstituted nitroalkenes via enantioselective protonation

254th National Meeting (2017)

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