Asymmetric NHC-catalyzed synthesis of alpha-fluoroamides from readily accessible alpha-fluoroenals

作者:Wheeler Philip; Vora Harit U; Rovis Tomislav*
来源:Chemical Science, 2013, 4(4): 1674-1679.
DOI:10.1039/c3sc00089c

摘要

The scope of the NHC-redox amidation has been expanded to include a variety of alpha,beta-unsaturated aldehydes, including alpha-fluoro alpha,beta-unsaturated aldehydes which give rise to enantioenriched alpha-fluoroamides in good to excellent yield and enantioselectivity (up to 97% ee). Enantioenriched amines may be elaborated to either diastereomer of the product in high diastereoselectivity (up to 99 : 1). Functionalization of the amide products to amines and fluorohydrins is also demonstrated with retention of enantioenrichment at the fluorine stereocenter.

  • 出版日期2013