Abstract
Conjugated cyclic trienes without nonbenzenoid aromatic characteristic were successfully employed as fine-tunable dipolarophiles in the Cu(I)-catalyzed asymmetric azomethine ylide-involved 1,3-dipolar [3 + 6] cycloaddition for the first time, affording a variety of bridged heterocycles bearing piperidine moiety in good yield with exclusive regioselectivity and excellent stereoselectivity. 2-Acyl group is the key factor that determines the annulation preferentially through [3 + 6]-pathway, while 2-ester group modulates the annulation through [3 + 2]-pathway.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Azo Compounds / chemical synthesis*
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Azo Compounds / chemistry
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Catalysis
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Cyclization
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Cycloheptanes / chemical synthesis*
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Cycloheptanes / chemistry
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry
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Molecular Conformation
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Organometallic Compounds / chemistry*
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Piperidines / chemistry*
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Thiosemicarbazones / chemical synthesis*
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Thiosemicarbazones / chemistry
Substances
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Azo Compounds
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Cycloheptanes
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Heterocyclic Compounds
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Organometallic Compounds
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Piperidines
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Thiosemicarbazones
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azomethine
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piperidine