Abstract
A one-step, three-component condensation of allenyl boronic acids or allenyl pinacolboronates with amines and aldehydes affords α-allenyl or α-propargyl α-amino acids and anti-β-amino alcohols. This process gives the allenyl or propargyl product depending on the amine and boron components. Secondary amines generate exclusively α-allenyl α-amino acids, while primary aliphatic amines lead to α-propargyl α-amino acids. Secondary aliphatic amines react with chiral α-hydroxy aldehydes and allenyl boron derivatives to form stereoselectively allenyl anti-β-amino alcohol products.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry*
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Alkynes / chemical synthesis*
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Alkynes / chemistry*
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Amines / chemistry*
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Amino Alcohols / chemical synthesis*
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Amino Alcohols / chemistry*
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Boron Compounds / chemical synthesis*
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Boron Compounds / chemistry*
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Boronic Acids / chemistry*
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Catalysis
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Molecular Structure
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Propanols / chemical synthesis*
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Propanols / chemistry*
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Stereoisomerism
Substances
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4,4,5,5-tetramethyl(1,3,2)dioxaborolane
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Aldehydes
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Alkynes
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Amines
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Amino Alcohols
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Boron Compounds
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Boronic Acids
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Propanols
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propargyl alcohol