Gold(I)‐Assisted α‐Allylation of Enals and Enones with Alcohols | Zendy

Mastandrea Marco Michele | Zendy; Mellonie Niall | Zendy; Giacinto Pietro | Zendy; Collado Alba | Zendy; Nolan Steven P. | Zendy; Miscione Gian Pietro | Zendy; Bottoni Andrea | Zendy; Bandini Marco | Zendy

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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

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.

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