Enolates are a ubiquitous carbon-carbon bond forming reaction which has been widely explored in the area of organic synthesis.  Enolates are generally formed using strongly basic media to form products, such as those found in aldol or Claissen reactions.  Generating enolates using milder conditions has a broader application, given the probability of a strongly basic reagent having side-reactions with a compound.<br/>The current project reacts a substituted oxetane with a substituted titanocene to form an oxetane.  The starting substituted lactones was obtained commercially and transformed to a methylene-substituted oxteane using dibenzyltitanocene. The oxetane was then treated with boron trifluoride and lithium bromide to facilitate ring-opening and reaction with three electrophiles: acetaldehyde, 1-bromobutane and 4-chlorobenzaldehyde.

Non-basic enolate generation by way of substituted oxetanes

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