Abstract
Herein, we describe the rhodium-catalyzed C-H amination reaction of 1,2-boryl sulfamate esters derived from amphoteric α-boryl aldehydes. Depending on the substitution pattern of the boryl sulfamate ester, a diverse range of five- or six-membered ring heterocycles are accessible using this transformation. The highly chemoselective nature of the C-H functionalization reaction preserves the alkyl boronate functional group, which enables the synthesis of B-C-N and B-C-C-N motifs that are present in a number of hydrolase inhibitors.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Amination
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Boronic Acids / chemical synthesis*
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Boronic Acids / chemistry
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Catalysis
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Esters
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Hydrolases / antagonists & inhibitors
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Hydrolases / chemical synthesis
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Hydrolases / chemistry
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Molecular Structure
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Rhodium / chemistry*
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Stereoisomerism
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Sulfonic Acids / chemistry*
Substances
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Aldehydes
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Boronic Acids
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Enzyme Inhibitors
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Esters
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Sulfonic Acids
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sulfamic acid
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Rhodium
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Hydrolases