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Enamines as Surrogates of Alkyl Carbanions for the Direct Conversion of Secondary Amides to α‐Branched Ketones
Author(s) -
Liu YongPeng,
Wang ShuRen,
Chen TingTing,
Yu CunCun,
Wang AiE,
Huang PeiQiang
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801443
Subject(s) - chemistry , carbanion , alkyl , alkylation , organic chemistry , electrophile , reagent , yield (engineering) , catalysis , materials science , metallurgy
A direct transformation of secondary amides into α‐branched ketones with enamines as soft alkylation reagents was developed. In this reaction, enamines serve as surrogates of alkyl carbanions, rather than the conventional enolates equivalents in the Stork's reactions, which allowed for the easy introduction of alkyl groups with electrophilic functional groups. In the presence of 4 Å molecular sieves, the method can be extended to the one‐pot coupling of secondary amides with aldehydes to yield ketones.