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Publication Detail
Stereoselective synthesis of 1,2-diamine containing indolines by a conjugate addition nitro-Mannich reaction.
  • Publication Type:
    Journal article
  • Publication Sub Type:
    Journal Article
  • Authors:
    Anderson JC, Campbell IB, Campos S, Shannon J, Tocher DA
  • Publication date:
    07/01/2015
  • Pagination:
    170, 177
  • Journal:
    Org Biomol Chem
  • Volume:
    13
  • Issue:
    1
  • Status:
    Published
  • Country:
    England
  • Language:
    eng
  • Keywords:
    Chemistry Techniques, Synthetic, Cyclization, Diamines, Indoles, Nitro Compounds, Palladium, Stereoisomerism, Substrate Specificity
Abstract
A conjugate addition nitro-Mannich reaction followed by nitro reduction and intramolecular N-arylation gives diastereomerically pure substituted 1,2-diamine containing indolines. Placing the N-arylation cyclisation handle on the imine precursor derived from an ortho-bromine substituted aromatic aldehyde gave the corresponding β-nitroamines in 55-72% yields as single diastereoisomers. Nitro reduction was effected with modified quantities of Zn/HCl and a subsequent Pd(0) catalysed Buchwald Hartwig cyclisation gave indoline products in 40-70% yields as single diastereoisomers.
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