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Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza‐Heterocycles |
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| Authors: | Dr. Sabin Llona‐Minguez Dr. Matthieu Desroses Artin Ghassemian Dr. Sylvain A. Jacques Dr. Lars Eriksson Rebecka Isacksson Tobias Koolmeister Dr. Pål Stenmark Dr. Martin Scobie Prof. Thomas Helleday |
| Affiliation: | 1. 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;2. Department of Materials and Environmental Chemistry, Stockholm University, Stockholm, 106 91 (Sweden);3. Department of Biochemistry and Biophysics, Stockholm University, Stockholm, 106 91 (Sweden) |
| 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. |
| Keywords: | aminophosphonate boronate cyclization heterocycles MIDA nitrene |