Asymmetric Claisen rearrangements on chiral vinyl sulfoxides. 2009

Roberto Fernández de la Pradilla, and Carlos Montero, and Mariola Tortosa, and Alma Viso
Instituto de Química Orgánica General, C.S.I.C. Juan de la Cierva 3, 28006 Madrid, Spain.

Highly diastereoselective Claisen rearrangements of acyclic allyl vinyl ethers bearing a chiral sulfoxide at C-5 provide gamma-delta-unsaturated aldehydes or ketones with up to two consecutive asymmetric centers in the molecule whilst preserving a useful vinyl sulfoxide. The reactivity of related vinyl sulfides and sulfones has also been examined in this work.

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