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Publication Detail
Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes
  • Publication Type:
    Journal article
  • Publication Sub Type:
    Article in Press
  • Authors:
    Anderson JC, Kalogirou AS, Tizzard GJ
  • Publisher:
    Elsevier Ltd
  • Publication date:
    19/08/2014
  • Journal:
    Tetrahedron
  • Status:
    Accepted
  • Print ISSN:
    0040-4020
  • PII:
    S0040-4020(14)01481-1
  • Language:
    eng
  • Keywords:
    Conjugate addition, Contiguous stereocentres, Diastereoselective, Nitro-Mannich reaction, Nitroalkenes
Abstract
The conjugate addition nitro-Mannich reactions of ethyl-β-nitroacrylate (1) and β-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conjugate addition nitro-Mannich reaction was unsuccessful except for the addition of alkoxides to 2 in alcohol as solvent. Isolation of the conjugate addition products followed by deprotonation with n BuLi and treatment with a simple imine in the presence of TFA led to β-nitroamine derived products. Products derived from 1 spontaneously cyclised in only a few examples and on the whole led to inherently unstable products. Products derived from 2 were isolated as their trifluoroacetamides, gave good yields of single diastereoisomers for aromatic and alkoxide nucleophiles and the structures were verified by single crystal X-ray crystallography. Products derived from amine nucleophiles were isolated in low yields while sulfur nucleophiles gave poor diastereoselectivities.
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