title: A Four-Component Reaction for the Synthesis of Dioxadiazaborocines.
abstract: A four-component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α-hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines). In this remarkable process, one boronic acid reacts as a carbon nucleophile and the other as a boron electrophile to provide enantio- and diastereomerically pure heterocyclic boronates with multiple stereocenters in high yields.
authors.affiliation: Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby (Denmark).
authors.forename: Thomas
authors.initials: T
authors.lastname: Flagstad
authors.affiliation: Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby (Denmark).
authors.forename: Mette T
authors.initials: MT
authors.lastname: Petersen
authors.affiliation: Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby (Denmark). ten@kemi.dtu.dk.|Singapore Centre on Environmental Life Sciences Engineering, Nanyang Technological University, Singapore 637551 (Singapore). ten@kemi.dtu.dk.
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Nielsen
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization
chemical_list: D000447:Aldehydes; D001897:Boronic Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic
keywords: boron; cyclization; heterocycles; multicomponent reactions; synthetic methods