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Bio‐inspired Domino oxa‐Michael/Diels–Alder/oxa‐Michael Dimerization of para ‐Quinols
Author(s) -
Green Nicholas J.,
Connolly Catherine A.,
Rietdijk Koen P. W.,
Nichol Gary S.,
Duarte Fernanda,
Lawrence Andrew L.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201802125
Subject(s) - stereocenter , michael reaction , pyrrolidine , domino , chemistry , diels–alder reaction , stereochemistry , organic chemistry , catalysis , enantioselective synthesis
A bio‐inspired, pyrrolidine‐mediated, dimerization of para ‐quinols has been developed. It represents one of the most complex, yet general, dimerization reactions ever disclosed, selectively forming four new bonds, four new rings, and eight new contiguous stereogenic centres. The para ‐quinol starting materials are easily handled, bench‐stable compounds, accessed in just one step from aromatic feedstocks. The reaction can be scaled up to give grams of polycyclic material, primed for further elaboration.