N-Tosylimidates in highly enantioselective organocatalytic Michael reactions |
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Authors: | Antonio Massa |
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Affiliation: | The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States |
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Abstract: | N-Tosylimidates acted as nucleophiles in highly enantioselective organocatalytic Michael addition reactions to α,β-unsaturated aldehydes in the presence of a catalytic amount of trialkylsilyl-protected diarylprolinol. In particular, α-phenyl-substituted N-tosylimidates showed good reactivity. We also demonstrate that the kinetic acidity of the α-proton of α-phenyl N-tosylimidate as measured by proton/deuterium NMR exchange experiments is correlated with the potential of N-tosylimidates to act as nucleophiles in organocatalytic reactions. |
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