Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides | Zendy

Daniel Kaiser | Zendy; Christopher J. Teskey | Zendy; Pauline Adler | Zendy; Nuno Maulide | Zendy

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Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides

Author(s) -

Daniel Kaiser,

Christopher J. Teskey,

Pauline Adler,

Nuno Maulide

Publication year - 2017

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.7b08813

Subject(s) - chemistry , umpolung , electrophile , intermolecular force , nucleophile , amide , chemoselectivity , functional group , catalysis , coupling (piping) , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , molecule , mechanical engineering , polymer , engineering

A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung via N-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolates. The method conveys broad functional group tolerance on both components, does not suffer from formation of homocoupling byproducts and avoids the use of transition metal catalysts.

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