Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 14-15, Pages 3091-3097Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500481
Keywords
aldol reaction; Brook rearrangement; fluorine; organocatalysis; stereogenic centers
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Funding
- Ecole Nationale Superieure de Chimie de Montpellier
- Centre National de la Recherche Scientifique
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A methodology allowing the preparation of aldols featuring a fluorinated stereogenic center is reported. The corresponding fluoroenolates are formed in situ from stable beta,beta-difluoro-alpha-(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.
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