Synfacts 2011(4): 0428-0428  
DOI: 10.1055/s-0030-1259605
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Polarity Inversion of Ketones: Umpolung Reaction at the α-Position

Contributor(s): Paul Knochel, Thomas Kunz
T. Miyoshi, T. Miyakawa, M. Ueda, O. Miyata*
Kobe Pharmaceutical University, Japan
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18. März 2011 (online)


This work discloses a protocol for the α-alkylation and α-arylation of ketones via an umpolung reaction under mild reaction conditions. The intermediate N-alkoxyenamine reacts directly with a wide range of organoaluminum reagents. This avoids the use of expensive transition-metal catalysis and high reaction temperatures often required for such reactions.