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Diastereoselective 1,4-Addition of Asymmeric Lithium Amides
S. A. Bentley, S. G. Davies*, J. A. Lee, P. M. Roberts, J. E. Thomson
University of Oxford, UK
20 July 2011 (online)
The authors describe the addition of N-aryl-N-(α-methyl)benzylamide 1 to α,β-unsaturated-4-methoxyphenyl esters 2. While this reactivity is well established (see Review), this is a first example of an N-aryl-substituted nucleophile. The utility of the products is established through the synthesis of a tetrahydroquinoline alkaloid through Friedel-Crafts reaction.
Review: S. G. Davies, A. D. Smith, P. D. Price Tetrahedron: Asymmetry 2005, 16, 2833-2891.