期刊
SYNLETT
卷 30, 期 15, 页码 1835-1839出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690133
关键词
acyloxyacroleins; 1,3-dipolar cycloaddition; isoxazolidines; nitrones; organocatalysis; asymmetric catalysis
Organoammonium salts of dipeptide-derived chiral tri-amines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of alpha-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 alpha-(p-methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, alpha-(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.
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