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Tuning the Reactivity of Functionalized Diallylic Alcohols: Brønsted versus Lewis Acid Catalysis
Author(s) -
Lempenauer Luisa,
Duñach Elisabet,
Lemière Gilles
Publication year - 2017
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.201702601
Subject(s) - reactivity (psychology) , chemistry , catalysis , bifunctional , brønsted–lowry acid–base theory , lewis acids and bases , lewis acid catalysis , thioether , organic chemistry , alcohol , enol , trifluoromethanesulfonate , combinatorial chemistry , medicinal chemistry , medicine , alternative medicine , pathology
The chemodivergent reactivity of bifunctional, enol thioether‐containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Brønsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov‐type electrocyclization, whereas activation of the thioenol ether by p ‐toluenesulfonic acid provides an entry to α‐sulfenylated β,γ‐unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non‐toxic catalytic systems.