Abstract
The enantioselective synthesis of α-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted α-positions. Broad functional group tolerance was explored at the α-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds.
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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Alkylation
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Catalysis
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Combinatorial Chemistry Techniques
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Heterocyclic Compounds, 1-Ring / chemical synthesis*
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Heterocyclic Compounds, 1-Ring / chemistry
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Ketones / chemical synthesis*
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Ketones / chemistry
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Molecular Structure
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Morpholines / chemical synthesis
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Morpholines / chemistry
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Oxazepines / chemical synthesis
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Oxazepines / chemistry
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Oxazolidinones / chemical synthesis
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Oxazolidinones / chemistry
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Palladium / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Heterocyclic Compounds, 1-Ring
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Ketones
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Morpholines
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Oxazepines
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Oxazolidinones
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Palladium