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A Four-Component Reaction for the Synthesis of Dioxadiazaborocines
Thomas Flagstad1, Mette T Petersen1, Thomas E Nielsen2,3
1Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby (Denmark).
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.
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