title: Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles.
abstract: A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.
authors: Science for Life Laboratory, Division of Translational, Medicine & Chemical Biology, Department of Medical Biochemistry & Biophysics, Karolinska Institutet, Stockholm, 171 21 (Sweden) http://www.helleday.org. sabin.llona.minguez@scilifelab.se.
authors: Sabin
authors: S
authors: Llona-Minguez
authors: Matthieu
authors: M
authors: Desroses
authors: Artin
authors: A
authors: Ghassemian
authors: Sylvain A
authors: SA
authors: Jacques
authors: Lars
authors: L
authors: Eriksson
authors: Rebecka
authors: R
authors: Isacksson
authors: Tobias
authors: T
authors: Koolmeister
authors: Pål
authors: P
authors: Stenmark
authors: Martin
authors: M
authors: Scobie
authors: Thomas
authors: T
authors: Helleday
keywords: MIDA; aminophosphonate; boronate; cyclization; heterocycles; nitrene