Abstract
A stereoselective and high-yield synthesis of hexahydropyrrolo[3,4-b]pyrroles from tetramic acids and 2H-azirines under Cu(I)-NHC catalysis is developed. An unusual N-C2 azirine bond cleavage, initiated by a copper enolate, was rationalized in terms of a free radical reaction mechanism.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Azirines / chemistry*
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Catalysis
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Copper / chemistry*
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Iodides / chemistry*
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Molecular Structure
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Pyrrolidinones / chemistry*
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Stereoisomerism
Substances
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Azirines
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Iodides
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Pyrroles
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Pyrrolidinones
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tetramic acid
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Copper
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cuprous iodide