Tandem Asymmetric Reactions

Tandem reactions that form relatively complex molecules with high levels of selectivity in a single step may be more efficacious than multi-step syntheses requiring several work-up and purification procedures. We have utilised the conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to promote the formation of polyfunctionalised 4-aminotetrahydroquinoline-3-carboxylic acid derivatives in a subsequent Mannich reaction.
 

 Tandem conjugate addition/cyclisation
 

Key Publications: 

  1. A tandem conjugate addition/cyclisation protocol for the asymmetric synthesis of 2-aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives
    Davies, S. G.; Mujtaba, N.; Roberts, P. M.; Smith, A. D.; Thomson, J. E. Org. Lett. 2009, 11, 1959
    [View Journal Page]
  2. Cyclic β-amino acid derivatives: synthesis via lithium amide promoted tandem asymmetric conjugate addition–cyclisation reactions
    Davies, S. G.; Diez, D.; Dominguez, S. H.; Garrido, N. M.; Kruchinin, D.; Price, P. D.; Smith, A. D. Org. Biomol. Chem. 2005, 3, 1284 [View Journal Page]









     

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