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.
Supporting Information
Experimental procedures and spectroscopic data for new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.
