Bifunctional (Thio)urea-Phosphine Organocatalysts Derived from d-Glucose and -Amino Acids and Their Application to the Enantioselective Morita-Baylis-Hillman Reaction

Abstract

Novel (thio)urea-tertiary phosphines were developed for use as bifunctional organocatalysts readily available from naturally occurring molecules: saccharides and amino acids. The efficiency of the organocatalysts was demonstrated in the asymmetric Morita-Baylis-Hillman (MBH) reaction of aromatic aldehydes with acrylates.

The MBH products were obtained in good yields (up to 85%) and with high enantioselectivities (up to 87% ee).

Keywords

• organocatalysis
• Morita-Baylis-Hillman reactions
• phosphines
• amino acids
• asymmetric catalysis