Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 21, Pages 3118-3125Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201601149
Keywords
asymmetric catalysis; ketones; Mannich reaction; nitrogen heterocycles; organocatalysis
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Funding
- National Natural Science Foundation of China [U1404211]
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Aryl ketones represent problematic substrates for asymmetric Mannich reactions due to a large steric hindrance exhibited by such compound species. A highly enantioselective direct Mannich reaction of aryl methyl ketones with cyclic imine benzo[e][1,2,3]oxathiazine 2,2-dioxides could be successfully carried out utilizing a combination of cinchona alkaloid-derived primary amines with trifluoroacetic acid (TFA); the primary amines feature a superior catalytic efficacy over secondary amines with a variety of sterically hindered carbonyl compounds as substrates. The reaction proceeded well with various cyclic imines in 89-97% ee and with various aryl methyl ketones in 85-98% ee. Moreover, the aryl carbonyl of a Mannich product could be transformed to ketoxime, which further undergoes a Beckmann rearrangement to produce an amide compound while maintaining enantioselectivity.
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