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Nucleophilic α‐Arylation and α‐Alkylation of Ketones by Polarity Inversion of N ‐Alkoxyenamines: Entry to the Umpolung Reaction at the α‐Carbon Position of Carbonyl Compounds
Author(s) -
Miyoshi Tetsuya,
Miyakawa Takayuki,
Ueda Masafumi,
Miyata Okiko
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201004374
Subject(s) - umpolung , enamine , alkylation , chemistry , nucleophile , organic chemistry , ketone , combinatorial chemistry , catalysis
A new aspect of enamine chemistry : The formation of N ‐alkoxyenamines from ketones has led to an efficient umpolung reaction. The alkylation of N ‐alkoxyenamines with trialkylaluminum compounds proceeded smoothly and gave α‐alkylated ketones (see scheme). This reaction offers a simple transformation of ketones into α‐substituted ketones without the need to isolate enamines and intermediary imines.