Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza‐Heterocycles. Issue 20 (25th March 2015)

• Record Type: Journal Article
• Authors: Llona‐Minguez, Sabin; Desroses, Matthieu; Ghassemian, Artin; Jacques, Sylvain A.; Eriksson, Lars; Isacksson, Rebecka; Koolmeister, Tobias; Stenmark, Pål; Scobie, Martin; Helleday, Thomas
• Is Part Of: Chemistry. Volume 21:Issue 20(2015)
• Page Start: 7394
• Page End: 7398
• Publication Date: 2015-03-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201406549
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A two‐step synthesis of structurally diverse pyrrole‐containing bicyclic systems is reported. <italic>ortho</italic>‐Nitro‐haloarenes coupled with vinylic <italic>N</italic>‐methyliminodiacetic acid (MIDA) boronates generate <italic>ortho</italic>‐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 <italic>ortho</italic>‐nitro‐allylarene derivative furnished a cyclic β‐aminophosphonate motif.</p> </abstract>