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Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza‐Heterocycles
Author(s) -
LlonaMinguez Sabin,
Desroses Matthieu,
Ghassemian Artin,
Jacques Sylvain A.,
Eriksson Lars,
Isacksson Rebecka,
Koolmeister Tobias,
Stenmark Pål,
Scobie Martin,
Helleday Thomas
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406549
Subject(s) - pyrrole , nitrene , nitro , chemistry , bicyclic molecule , combinatorial chemistry , ring (chemistry) , molecule , substrate (aquarium) , stereochemistry , derivative (finance) , organic chemistry , catalysis , alkyl , oceanography , geology , financial economics , economics
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.