A Four‐Component Reaction for the Synthesis of Dioxadiazaborocines

Thomas Flagstad, Mette Terp Petersen, Thomas E. Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

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.
Original languageEnglish
JournalAngewandte Chemie International Edition
Volume54
Issue number29
Pages (from-to)8395-8397
Number of pages3
ISSN1433-7851
DOIs
Publication statusPublished - 2015

Keywords

  • Boron
  • Cyclization
  • Heterocycles
  • Multicomponent reactions
  • Synthetic methods

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