One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System
Identifieur interne : 000992 ( Main/Exploration ); précédent : 000991; suivant : 000993One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System
Auteurs : Alice Devineau ; Guillaume Pousse [France] ; Catherine Taillier ; Jérôme Blanchet [France] ; Jacques Rouden [France] ; Vincent DallaSource :
- Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2010-11-22.
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Abstract
A new sequential two‐step multicatalytic strategy is presented consisting in the efficient DBU‐catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)‐catalysed intermolecular alkylation by silicon‐based nucleophiles and CH nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one‐pot Brønsted base‐Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.
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DOI: 10.1002/adsc.201000602
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The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. 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