A four-component reaction for the synthesis of dioxadiazaborocines

• Main Authors: Flagstad, Thomas, Petersen, Mette Terp, Nielsen, Thomas Eiland
• Other Authors: Singapore Centre for Environmental Life Sciences Engineering
• Format: Article
• Language: English
• Published: 2015
• Subjects: DRNTU::Science::Chemistry
• Online Access: https://hdl.handle.net/10356/105983; http://hdl.handle.net/10220/26036; http://dx.doi.org/10.1002/anie.201502989
• Institution: Nanyang Technological University

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.