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@ARTICLE{Weber:885456,
author = {Weber, Anja and Breugst, Martin and Pietruszka, Jörg},
title = {{E}xperimental and {C}omputational {I}nvestigations of the
{R}eactions between α,β‐{U}nsaturated {L}actones and
1,3‐{D}ienes by {C}ooperative {L}ewis {A}cid/{B}rønsted
{A}cid {C}atalysis},
journal = {Angewandte Chemie / International edition},
volume = {59},
number = {42},
issn = {1521-3773},
address = {Weinheim},
publisher = {Wiley-VCH},
reportid = {FZJ-2020-03839},
pages = {18709 - 18716},
year = {2020},
abstract = {The reactions of α,β‐unsaturated δ‐lactones with
activated dienes such as
1,3‐dimethoxy‐1‐[(trimethylsilyl)oxy]‐1,3‐butadiene
(Brassard's diene) are barely known in literature and show
high potential for the synthesis of isocoumarin moieties. An
in‐depth investigation of this reaction proved a stepwise
mechanism via the vinylogous Michael‐products. Subsequent
cyclisation and oxidation by LHMDS and DDQ, respectively,
provided six mellein derivatives $(30–84 \%)$ and four
angelicoin derivatives $(40–78 \%)$ over three steps.
DFT‐calculations provide insights into the reaction
mechanism and support the theory of a stepwise reaction.},
cin = {IBOC / IBG-1},
ddc = {540},
cid = {I:(DE-Juel1)IBOC-20090406 / I:(DE-Juel1)IBG-1-20101118},
pnm = {581 - Biotechnology (POF3-581)},
pid = {G:(DE-HGF)POF3-581},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:32567075},
UT = {WOS:000559994400001},
doi = {10.1002/anie.202008365},
url = {https://juser.fz-juelich.de/record/885456},
}