(Matrix presented) β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3, 3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α -methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry