Abstract
Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p -methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.
Original language | English |
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Pages (from-to) | 1835-1839 |
Number of pages | 5 |
Journal | Synlett |
Volume | 30 |
Issue number | 15 |
DOIs | |
Publication status | Published - 2019 |
Keywords
- 1,3-dipolar cycloaddition
- acyloxyacroleins
- asymmetric catalysis
- isoxazolidines
- nitrones
- organocatalysis
ASJC Scopus subject areas
- Organic Chemistry