Synfacts 2011(8): 0872-0872  
DOI: 10.1055/s-0030-1260829
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective 1,4-Addition of Asymmeric Lithium Amides

Contributor(s): Mark Lautens, Jane Panteleev
S. A. Bentley, S. G. Davies*, J. A. Lee, P. M. Roberts, J. E. Thomson
University of Oxford, UK
Further Information

Publication History

Publication Date:
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.