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Diastereoselective, One‐Pot Synthesis of Polyfunctionalized Bicyclo[3.3.1]nonanes by an Anionic Domino Process
Author(s) -
Barboni Luciano,
Gabrielli Serena,
Palmieri Alessandro,
Femoni Cristina,
Ballini Roberto
Publication year - 2009
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.200900366
Subject(s) - domino , bicyclic molecule , acrylate , chemistry , cascade reaction , organic chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , catalysis , polymer , monomer
One pot, many reactions! The reaction of two equivalents of ethyl(2‐bromomethyl)acrylate with dinitroalkanes (see scheme) leads to the one‐pot, diastereoselective synthesis of a variety of polyfunctionalized bicyclo[3.3.1]nonanes in very good overall yields. The reaction proceeds through an anionic domino process, with the in situ generation of four new CC bonds.