1,1-Dimetallic reagents for the elaboration of stereoselectively di- or trisubstituted linear substrates.
Although gem-dimetallic species have been known for a long time, and reacted once or twice with electrophiles, the allyl zincation of substituted vinyl metals has emerged as a particularly efficient access to such species. This is due to a high face selectivity, in the addition to the C=C bond, which can be governed by vicinal or more remote heteroatoms. This strategy has some aspects in common with the well-known allylations or aldol condensations to carbonyl derivatives. But in the present case, the C=C bond has a low polarity. We present here some examples which lead to di- or polysubstituted linear substrates, of given geometry, where the organodimetallic obtained has been doubly protonated by water. Further elaborations (to alkenes, ketones, etc.) are possible.
Normant
J F
JF
Laboratoire de Chimie des Organoéléments, Université Pierre et Marie Curie, 4 Place Jussieu-Tour 44, 75252 Paris Cedex 05, France. normant@moka.ccr.jussieu.fr