Asymmetric Allylation Using COP Catalysts

By: William Sommer, Aldrich ChemFiles 2008, 8.6, 6.

Aldrich ChemFiles 2008, 8.6, 6.

Chiral allylic aryl esters are valuable building blocks for the synthesis of natural products and drug candidates. In recent years, several research groups developed new catalysts to synthesize chiral allylic esters from phenols and prochiral allylic precursors.1 Overman and co-workers developed a new method to synthesize chiral 3-aryloxy-1-alkenes using COP-OAc catalysts.2 This reaction only requires 1 mol% of catalyst producing the desired product in high yields and high ee’s (Scheme 1). A library of alllylic trichloroacetimidates and phenols were screened. This new method is compatible with the presence of base-labile functionality.

Scheme 1.

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  1. (a) Trost, B. et al. J. Am. Chem. Soc. 2005, 127, 7014. (b) Mbaye, M. D. Et al. Chem. Commun. 2004, 1870. (c) Shekhar, S. et al. J. Am. Chem. Soc. 2006, 128, 11770.
  2. Kirsch, S. F. Et al. Org. Lett. 2007, 9, 911.

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