A Four‐Component Reaction for the Synthesis of Dioxadiazaborocines1. (9th June 2015)

• Record Type: Journal Article
• Authors: Flagstad, Thomas; Petersen, Mette T.; Nielsen, Thomas E.
• Is Part Of: Angewandte Chemie. Volume 127:Number 29(2015)
• Page Start: 8515
• Page End: 8517
• Publication Date: 2015-06-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201502989
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>