title: Component-selective and stereocontrolled one-step three-component reaction among aldehydes, amines, and allenyl boronic acids or allenyl pinacolboronates.
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.
authors: Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, California 90089, United States.
authors: Fotini
authors: F
authors: Liepouri
authors: Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, California 90089, United States.
authors: Giovanni
authors: G
authors: Bernasconi
authors: Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, California 90089, United States.
authors: Nicos A
authors: NA
authors: Petasis
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C578864:4,4,5,5-tetramethyl(1,3,2)dioxaborolane; D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D000605:Amino Alcohols; D001896:Boron Compounds; D001897:Boronic Acids; D020005:Propanols; C028255:propargyl alcohol