Lithium Amide Conjugate Addition Methodology

Chiral lithium amides have been extensively used and studied within organic synthesis as effective reagents for a range of transformations including enantioselective reduction, alkylation, deprotonation, desymmetrisation and kinetic resolution. Although many of these procedures rely upon lithium amides to act as chiral bases, lithium amides may also act as nucleophiles. Within this arena, we have shown that the conjugate addition of a range of secondary lithium amides, derived from enantiopure α-methylbenzylamine, to α,β-unsaturated esters represents an efficient method for the preparation of β-amino esters and their derivatives. We have exploited this reaction in a range of synthetic applications, including the initiation of tandem asymmetric processes, enantiorecognition phenomena, and total synthesis.


Key Publications: 

  1. Solution phase structures of enantiopure and racemic lithium N-benzyl-N-(α-methylbenzyl)amide in THF: low temperature 6Li and 15N NMR spectroscopic studies
    Claridge, T. D. W.; Davies, S. G.; Kruchinin, D.; Odell, B.; Roberts, P. M.; Russell, A. J.; Thomson, J. E.; Toms, S. M. Tetrahedron: Asymmetry 2013, 24, 947 [View Journal Page]
  2. Asymmetric syntheses of dihydroxyhomoprolines via doubly diastereoselective lithium amide conjugate addition reactions
    Davies, S. G.; Foster, E. M.; Lee, J. A.; Roberts, P. M.; Thomson, J. E. Tetrahedron 201369, 8680 
    [View Journal Page]
  3. ​The conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents part II: 
    Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Thomson, J. E. Tetrahedron: Asymmetry 201223, 1111 
    [View Journal Page]





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