Synfacts 2008(9): 0981-0981  
DOI: 10.1055/s-2008-1078631
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

1,2-Rearrangement of α,α-Disubstituted α-Siloxy Aldehydes: Switchable Regioselectivity

Contributor(s): Paul Knochel, Tobias Thaler
K. Ohmatsu, T. Tanaka, T. Ooi, K. Maruoka*
Kyoto University, Japan
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

The regioselectivity of the 1,2-rearrangement reaction in α,α-disubstituted α-siloxy aldehydes can be switched either in favor of the transfer of the aryl or alkyl moiety depending on the nature of the Al catalyst and the respective conditions. In both cases the reactions proceed with good to excellent regioselectivities.