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ChemInform Abstract: Stereoselective Conjugate Addition Reactions of α,β-Unsaturated tert-Butyl Esters with Aryllithium Reagents.

✍ Scribed by L. F. FREY; R. D. TILLYER; A.-S. CAILLE; D. M. TSCHAEN; U. H. DOLLING; E. J. J. GRABOWSKI; P. J. REIDER

Publisher
John Wiley and Sons
Year
2010
Weight
42 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereoselective Conjugate Addition Reactions of α,β-Unsaturated tert-Butyl Esters with Aryllithium Reagents. -Aryllithium reagents undergo stereoselective 1,4-addition reactions to α,β-unsaturated tert-butyl esters bearing a chirally modified aryl substituent at C-3. Good selectivities are obtained by experimentally matching the non predictable chiral auxiliary and solvent effects. Due to the use of tert-butyl esters the competing formation of 1,2-addition products is minimized (¡5%). This protocol provides a practicable alternative to the reported conjugate addition reactions of Gilman-type cuprates to cinnamates. The investigation is presented with a view to the pharmaceutical importance of β,β-diaryl propionic acid derivatives. -(FREY, L.

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