Abstract
A natural product inspired synthesis of 6,6,5-tricyclic compounds via a silver(I)-catalyzed formal 1,3-dipolar cycloaddition of coumarins with α-iminoesters was developed. The reaction proceeds in a stepwise reaction course under formation of the trans-substituted diastereomer with respect to the 1,3-dipole and shows a broad substrate scope.
Keywords:
Azomethine ylide; Biology-oriented synthesis (BIOS); Catalysis; Coumarin; [2+3] cycloaddition.
Copyright © 2015 Elsevier Ltd. All rights reserved.
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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Benzopyrans / chemical synthesis*
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Benzopyrans / chemistry
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Coumarins / chemical synthesis
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Coumarins / chemistry*
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Cycloaddition Reaction
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Pyrrolidines / chemical synthesis*
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Pyrrolidines / chemistry
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Silver / 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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Benzopyrans
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Coumarins
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Pyrrolidines
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Thiosemicarbazones
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azomethine
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Silver
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coumarin