Abstract
Compound 20, a pseudoenantiomer of β-isocupreidine (β-ICD), was synthesized from quinine employing a Barton reaction of nitrosyl ester 13 and acid-catalyzed cyclization of carbinol 18 as key steps. The Baylis-Hillman reaction of benzaldehyde, p-nitrobenzaldehyde, and hydrocinnamaldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) using 20 as a chiral amine catalyst was found to give the corresponding S-enriched adducts in high optical purity (> 91% ee) in contrast to the β-ICD-catalyzed reaction which affords R-enriched adducts. This result suggests that compound 20 can serve as an enantiocomplementary catalyst of β-ICD in the asymmetric Baylis-Hillman reaction of aldehydes with HFIPA.
Original language | English |
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Pages (from-to) | 1790-1796 |
Number of pages | 7 |
Journal | Advanced Synthesis and Catalysis |
Volume | 347 |
Issue number | 14 |
DOIs | |
Publication status | Published - 2005 Nov 1 |
Externally published | Yes |
Keywords
- Asymmetric catalysis
- Baylis-Hillman reaction
- Organic catalysis
- Quinine
- β-isocupreidine
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry