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Asymmetric Claisen Rearrangements on Chiral Vinyl Sulfoxides
Author(s) -
Fernández de la Pradilla Roberto,
Montero Carlos,
Tortosa Mariola,
Viso Alma
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801680
Subject(s) - sulfoxide , claisen rearrangement , chemistry , reactivity (psychology) , dimethyl sulfoxide , organic chemistry , medicine , alternative medicine , pathology
Abstract Highly diastereoselective Claisen rearrangements of acyclic allyl vinyl ethers bearing a chiral sulfoxide at C‐5 provide γ‐ δ ‐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.