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Gold(I)‐Assisted α‐Allylation of Enals and Enones with Alcohols
Author(s) -
Mastandrea Marco Michele,
Mellonie Niall,
Giacinto Pietro,
Collado Alba,
Nolan Steven P.,
Miscione Gian Pietro,
Bottoni Andrea,
Bandini Marco
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507218
Subject(s) - silanes , allylic rearrangement , chemistry , nucleophile , yield (engineering) , enone , catalysis , nucleophilic addition , intermolecular force , condensation , organic chemistry , combinatorial chemistry , silane , molecule , materials science , physics , metallurgy , thermodynamics
Abstract The intermolecular α‐allylation of enals and enones occurs by the condensation of variously substituted allenamides with allylic alcohols. Cooperative catalysis by [Au(I t Bu)NTf 2 ] and AgNTf 2 enables the synthesis of a range of densely functionalized α‐allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an α‐gold(I) enal/enone as the active nucleophilic species.