Abstract
(3S,8S,9R)-3,9-Epoxy-6'-hydroxy-11-norcinconane (23), a pseudoenantiomer of β-isocupreidine (β-ICD), was synthesized starting with a fragmentation reaction of 10-bromo-10,11-dihydroquinine, prepared from quinine. Baylis-Hillman reaction of benzaldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) using 23 as a chiral amine catalyst gave the corresponding S-enriched adduct in high optical purity (93% ee) in contrast to the β-ICD-catalyzed reaction which affords R-enriched adducts.
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