Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals
2013; Royal Society of Chemistry; Volume: 4; Issue: 4 Linguagem: Inglês
10.1039/c3sc00089c
ISSN2041-6539
AutoresPhilip Wheeler, Harit U. Vora, Tomislav Rovis,
Tópico(s)Catalytic Cross-Coupling Reactions
ResumoThe scope of the NHC-redox amidation has been expanded to include a variety of α,β-unsaturated aldehydes, including α-fluoro α,β-unsaturated aldehydes which give rise to enantioenriched α-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.
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