Premium
A Four‐Component Reaction for the Synthesis of Dioxadiazaborocines
Author(s) -
Flagstad Thomas,
Petersen Mette T.,
Nielsen Thomas E.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502989
Subject(s) - stereocenter , chemistry , electrophile , nucleophile , boronic acid , component (thermodynamics) , boron , bicyclic molecule , organic chemistry , combinatorial chemistry , reactive intermediate , catalysis , enantioselective synthesis , physics , thermodynamics
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.