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Inside Back Cover: Synthesis of Polysubstituted γ‐Butenolides via a Radical Pathway: Cyclization of α‐Bromo Aluminium Acetals and Comparison with the Cyclization of α‐Bromoesters at High Temperature (Chem. Eur. J. 32/2015)
Author(s) -
Bénéteau Romain,
Despiau Carole F.,
Rouaud JeanChristophe,
Boussonnière Anne,
Silvestre Virginie,
Lebreton Jacques,
Dénès Fabrice
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201590145
Subject(s) - stereocenter , chemistry , radical cyclization , hydrogen atom , epimer , medicinal chemistry , aluminium , hydrogen , catalysis , stereochemistry , organic chemistry , enantioselective synthesis , alkyl
Polysubstituted γ‐butenolides were obtained by a one‐pot sequence that involves the radical cyclization of α‐bromo aluminium acetals under mild reaction conditions, followed by in situ oxidation. In their Full Paper on page 11378 ff. F. Dénès et al. compare this approach with the direct cyclization of α‐bromoesters at high temperature, for which side reactions were observed. Among these, hydrogen‐atom transfer (HAT) from the side‐chains, which have remained so far unnoticed during this type of cyclization, were brought to light by the epimerization of “unreactive” stereogenic centres.