Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β-Difluoro-α-(trimethylsilyl)alcohols - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2015

Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β-Difluoro-α-(trimethylsilyl)alcohols

Résumé

A methodology allowing the preparation of aldols featuring a fluorinated stereogenic center is reported. The corresponding fluoroenolates are formed in situ from stable β,β-difluoro-α-(trimethylsilyl)alcohols, through a base-mediated process involving a Brook rearrangement followed by a fluoride elimination, and are directly added to aromatic aldehydes. Two different sets of conditions were disclosed. The first one involves the stoichiometric addition of potassium tert-butoxide (t-BuOK) while the second is based on the use of a catalytic amount of an ammonium phenoxide. The latter opens the way for a catalytic and asymmetric version of this Brook/elimination/aldol reaction (BEAR) sequence.

Dates et versions

hal-01218532 , version 1 (21-10-2015)

Identifiants

Citer

M Decostanzi, Arie van Der Lee, Jean-Marc Campagne, Eric Leclerc. Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β-Difluoro-α-(trimethylsilyl)alcohols. Advanced Synthesis and Catalysis, 2015, 357 (14-15), pp.3091-3097. ⟨10.1002/adsc.201500481⟩. ⟨hal-01218532⟩
93 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More