ol5b00387_si_002.cif (14.89 kB)
A General, Scalable, Organocatalytic Nitro-Michael Addition to Enones: Enantioselective Access to All-Carbon Quaternary Stereocenters
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posted on 2016-01-11, 12:05 authored by Xiaodong Gu, Yuanyuan Dai, Tingting Guo, Allegra Franchino, Darren J. Dixon, Jinxing YeA tert-leucine-derived chiral diamine catalyzes
the asymmetric Michael addition of nitromethane to five-, six-, and
seven-membered β-substituted cyclic enones with excellent enantioselectivity,
offering scalable, asymmetric access to all-carbon quaternary stereocenters.
The reaction scope can be expanded to include linear acyclic enones,
and excellent levels of enantioselectivity are also observed. Furthermore,
this organocatalytic, asymmetric nitro-Michael reaction is amenable
to multigram scale-up and applications in the construction of an eudesmane
sesquiterpenoid skeleton.
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Organocatalyticenantioselectivitystereocenterdiaminecatalyzeacyclic enonesMichael additionmultigramoffering scalableScalableaccessapplicationnitromethaneEnoneorganocatalyticEnantioselective AccessQuaternaryreaction scopeStereocentersAchiralGeneralcyclic enonesconstructionquaternaryeudesmane sesquiterpenoid skeleton
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