Abstract
Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Aldehydes / chemistry*
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Alkenes / chemistry*
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Catalysis
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Chelating Agents / chemistry
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry*
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Ketones / chemical synthesis*
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Ketones / chemistry
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Molecular Structure
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Nitrogen / chemistry*
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Rhodium / chemistry*
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Stereoisomerism
Substances
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Aldehydes
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Alkenes
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Chelating Agents
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Heterocyclic Compounds
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Ketones
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Rhodium
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Nitrogen