Journal of Organic Chemistry 2007-11-09

Highly selective rhodium-catalyzed conjugate addition reactions of 4-oxobutenamides.

Jamie L Zigterman, Jacqueline C S Woo, Shawn D Walker, Jason S Tedrow, Christopher J Borths, Emilio E Bunel, Margaret M Faul

Index: J. Org. Chem. 72 , 8870, (2007)

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Abstract

A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to >99:1, >96% ee) and moderate to excellent yields (54-99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines, such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets by selective derivatization of either the amide or ketone functional group. A stereochemical model predicting the absolute sense of induction was developed based on single-crystal X-ray structures of product and precatalyst.

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