652146-28-6Relevant articles and documents
Efficient One-Step Aldol-Type Reaction of Ketones with Acetals and Ketals Mediated by Dibutylboron Triflate/ Diisopropylethyl Amine
Li, Lian-Sheng,Das, Sanjib,Sinha, Subhash C.
, p. 127 - 130 (2004)
(Equation presented) A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of β-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu2BOTf and i-Pr2NEt affording the products in high yields. Formation of the two possible diastereoisomers of the β-alkoxy ketones from the chiral acetals shows that the condensation takes place by an SN1 mechanism, involving prior opening of the acetal to an oxonium ion.