title: Boronic esters in asymmetric synthesis.
abstract: The author's work on (α-haloalkyl)boronic esters as reagents for asymmetric synthesis is reviewed. Diastereomeric ratios exceeding 1000 can be achieved with this chemistry, and ratios around 100 are commonplace. The method allows sequential installation of a series of stereocenters and tolerates a wide variety of suitably protected functional substituents. (α-Amidoalkyl)boronic acids include biochemically significant serine protease inhibitors, one of which is the clinically successful proteasome inhibitor bortezomib, used for treatment of multiple myeloma and mantle cell lymphoma.
authors.affiliation: Washington State University , Pullman, Washington 99164-4630, United States.
authors.forename: Donald S
authors.initials: DS
authors.lastname: Matteson
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D001895:Boron / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D004952:Esters; D007202:Indicators and Reagents / Q000737:chemistry*; D020522:Lymphoma, Mantle-Cell / Q000737:chemistry / Q000188:drug therapy; D015394:Molecular Structure; D009101:Multiple Myeloma / Q000737:chemistry / Q000188:drug therapy; D011480:Protease Inhibitors / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000588:Amines; D000970:Antineoplastic Agents; D001897:Boronic Acids; D004952:Esters; D007202:Indicators and Reagents; D011480:Protease Inhibitors; D001895:Boron